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University of Oxford
1.
Maciver, Eleanor E.
Asymmetric electrocyclic reactions.
Degree: PhD, 2013, University of Oxford
URL: http://ora.ox.ac.uk/objects/uuid:17ba3cb0-0c62-406a-bed4-14c410a45918
;
https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588436
► Pericyclic reactions are a class of transformations that comprise sigmatropic rearrangements, group transfer reactions, cycloadditions and electrocyclic reactions. Since Woodward and Hoffmann rationalized the mechanism…
(more)
▼ Pericyclic reactions are a class of transformations that comprise sigmatropic rearrangements, group transfer reactions, cycloadditions and electrocyclic reactions. Since Woodward and Hoffmann rationalized the mechanism and stereochemistry of pericyclic reactions they have become powerful synthetic tools. Whilst sigmatropic rearrangements and cycloadditions are cornerstones of contemporary synthetic methodology, many electrocyclic reactions are not fully exploited currently; there are no general methods for the asymmetric catalysis of electrocyclic reactions and as a consequence, opportunities for exerting stereocontrol in these manifolds are limited. We aim to establish general methods for the asymmetric catalysis of 6π electrocyclic reactions. Our initial studies are focused on a pentadienyl anion moiety due to the greater ease of cyclization observed with such systems in comparison to the corresponding neutral hexatriene systems.
Subjects/Keywords: 547; Asymmetric catalysis; Electrocyclization; Asymmetric; Catalysis
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Chicago ·
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APA (6th Edition):
Maciver, E. E. (2013). Asymmetric electrocyclic reactions. (Doctoral Dissertation). University of Oxford. Retrieved from http://ora.ox.ac.uk/objects/uuid:17ba3cb0-0c62-406a-bed4-14c410a45918 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588436
Chicago Manual of Style (16th Edition):
Maciver, Eleanor E. “Asymmetric electrocyclic reactions.” 2013. Doctoral Dissertation, University of Oxford. Accessed March 04, 2021.
http://ora.ox.ac.uk/objects/uuid:17ba3cb0-0c62-406a-bed4-14c410a45918 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588436.
MLA Handbook (7th Edition):
Maciver, Eleanor E. “Asymmetric electrocyclic reactions.” 2013. Web. 04 Mar 2021.
Vancouver:
Maciver EE. Asymmetric electrocyclic reactions. [Internet] [Doctoral dissertation]. University of Oxford; 2013. [cited 2021 Mar 04].
Available from: http://ora.ox.ac.uk/objects/uuid:17ba3cb0-0c62-406a-bed4-14c410a45918 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588436.
Council of Science Editors:
Maciver EE. Asymmetric electrocyclic reactions. [Doctoral Dissertation]. University of Oxford; 2013. Available from: http://ora.ox.ac.uk/objects/uuid:17ba3cb0-0c62-406a-bed4-14c410a45918 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588436

University of Notre Dame
2.
Eric C. Hansen.
Development and Applications of Quantum to Molecular
Mechanics (Q2MM)</h1>.
Degree: Chemistry and Biochemistry, 2017, University of Notre Dame
URL: https://curate.nd.edu/show/wd375t37h4h
► Asymmetric synthesis is a major focus in modern organic chemistry. Experimentally screening for selective ligands is a cumbersome process, and provides only indirect insight…
(more)
▼ Asymmetric synthesis is a major focus in
modern organic chemistry. Experimentally screening for selective
ligands is a cumbersome process, and provides only indirect insight
into the molecular origin of selectivity. Transition state force
fields generated by the Quantum to Molecular Mechanics (Q2MM)
method can describe the stereoselecting transition states involved
in reactions of interest to synthetic chemistry with the accuracy
of electronic structure methods but the speed of force field
calculations. This can provide structural and mechanistic
rationales for experimental observations and make quantitative
predictions before experimental ligand screening. This thesis
presents a robust code for performing Q2MM parameterization of
ground state and transition state force fields and improvements to
Q2MM. An automated virtual screening program is developed, which
works alongside Q2MM to rapidly perform virtual screens of ligands
in
asymmetric catalysis. The capabilities of Q2MM are demonstrated
in a study of the conformations of sulfones and sulfonamides, which
were investigated using high level electronic structure methods.
They revealed a dual anomeric effect, and the robustness of the
Q2MM method was demonstrated by parameterizing a force field that
implicitly captured these complicated electronic effects. Lastly,
the mechanism and structural origin of an unexpected
stereoselection observed in the rhodium catalyzed hydrogenation of
cyclic dehydrooligopeptides was studied using
Q2MM.
Advisors/Committee Members: Olaf Wiest, Research Director, Per-Ola Norrby, Committee Member, Jeffrey W. Peng, Committee Member, J. Daneil Gezelter, Committee Member.
Subjects/Keywords: Chemistry; Asymmetric catalysis
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APA (6th Edition):
Hansen, E. C. (2017). Development and Applications of Quantum to Molecular
Mechanics (Q2MM)</h1>. (Thesis). University of Notre Dame. Retrieved from https://curate.nd.edu/show/wd375t37h4h
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Hansen, Eric C.. “Development and Applications of Quantum to Molecular
Mechanics (Q2MM)</h1>.” 2017. Thesis, University of Notre Dame. Accessed March 04, 2021.
https://curate.nd.edu/show/wd375t37h4h.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Hansen, Eric C.. “Development and Applications of Quantum to Molecular
Mechanics (Q2MM)</h1>.” 2017. Web. 04 Mar 2021.
Vancouver:
Hansen EC. Development and Applications of Quantum to Molecular
Mechanics (Q2MM)</h1>. [Internet] [Thesis]. University of Notre Dame; 2017. [cited 2021 Mar 04].
Available from: https://curate.nd.edu/show/wd375t37h4h.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Hansen EC. Development and Applications of Quantum to Molecular
Mechanics (Q2MM)</h1>. [Thesis]. University of Notre Dame; 2017. Available from: https://curate.nd.edu/show/wd375t37h4h
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Brock University
3.
Zaifman, Joshua David.
Stereoselective synthesis of substituted hexahydro-3a,4a-diazacyclopentaphenanthren-4-ones and aminoferrocenes
.
Degree: Department of Chemistry, 2011, Brock University
URL: http://hdl.handle.net/10464/3383
► This thesis explored the development of several methodologies for the stereoselective construction of ligand frameworks and some of their applications. The first segment concerns the…
(more)
▼ This thesis explored the development of several methodologies for the
stereoselective construction of ligand frameworks and some of their applications. The
first segment concerns the application of an enantioselective lithiation at an Sp3_
hybridized position adjacent to nitrogen by means of the widely used and typically highly
effective enantioselective lithiation with ( -)-sparteine. This investigation was intended to
develop a method to install chirality into a system that would be converted into a family
of diaminoylidenes for use as phosphine mimics in transition metal catalysis or as
nucleophilic reagents. Molecular modeling of the system revealed some key interactions
between the substrate and (-)-sparteine that provided general insight into the diamine's
mode of action and should lend some predictive value to its future applications.
The second portion focuses on the development of methods to access 1,2-
disubstituted aminoferrocenes, an underexplored class of metallocenes possessing planar
chirality. Two routes were examined involving a diastereoselective and an
enantioselective pathway, where the latter method made use of the first BF3-mediated
lithiation-substitution to install planar chirality. Key derivatives such as 1,2-
aminophosphines, made readily accessible by the new route, were evaluated as ligands
for Pd(II), Pt(II) and Ir(I). These complexes show activity in a number of transformations
with both achiral and prochiral substrates. Optimization experiments were conducted to
prepare enantiomerically enriched 2-substituted-I-aminoferrocenes by direct asymmetric
lithiation of BF3-coordinated tertiary aminoferrocenes. A predictive computational model
describing the transition state of this reaction was developed in collaboration with
Professor Travis Dudding's group (Department of Chemistry, Brock University). The predicted stereochemistry of the process was confirmed by single-crystal X-ray analysis
of a 2-phosphino-l-dimethylaminoferrocene derivative. Enantiomerically pure samples of
the aminophosphine ligands derived from this new process have given promising
preliminary results in the enantioselective hydrogenation of prochiral alkenes and warrant
further stUdy in metal-mediated catalysis.
Subjects/Keywords: Asymmetric synthesis;
Catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Zaifman, J. D. (2011). Stereoselective synthesis of substituted hexahydro-3a,4a-diazacyclopentaphenanthren-4-ones and aminoferrocenes
. (Thesis). Brock University. Retrieved from http://hdl.handle.net/10464/3383
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Zaifman, Joshua David. “Stereoselective synthesis of substituted hexahydro-3a,4a-diazacyclopentaphenanthren-4-ones and aminoferrocenes
.” 2011. Thesis, Brock University. Accessed March 04, 2021.
http://hdl.handle.net/10464/3383.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Zaifman, Joshua David. “Stereoselective synthesis of substituted hexahydro-3a,4a-diazacyclopentaphenanthren-4-ones and aminoferrocenes
.” 2011. Web. 04 Mar 2021.
Vancouver:
Zaifman JD. Stereoselective synthesis of substituted hexahydro-3a,4a-diazacyclopentaphenanthren-4-ones and aminoferrocenes
. [Internet] [Thesis]. Brock University; 2011. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10464/3383.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Zaifman JD. Stereoselective synthesis of substituted hexahydro-3a,4a-diazacyclopentaphenanthren-4-ones and aminoferrocenes
. [Thesis]. Brock University; 2011. Available from: http://hdl.handle.net/10464/3383
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of St. Andrews
4.
Noonan, Gary M.
Asymmetric hydroformylation : a powerful tool for the synthesis of pharmaceutical intermediates
.
Degree: 2011, University of St. Andrews
URL: http://hdl.handle.net/10023/3105
► The hydroformylation of unfunctionalised olefins (such as prop-1-ene and oct-1-ene) is an extremely valuable process and is practised on a massive scale industrially in the…
(more)
▼ The hydroformylation of unfunctionalised olefins (such as prop-1-ene and oct-1-ene)
is an extremely valuable process and is practised on a massive scale industrially in the
synthesis of commodity chemicals. In fact, it represents the worlds largest scale
application of homogeneous
catalysis. As a result, the majority of research carried out
on this reaction has been in the study of catalytic systems which provide high rates
and selectivity for the production of linear aldehydes from terminal unfunctionalised
olefins, with the products finding use in the production of plasticizers and detergents.
Asymmetric hydroformylation, the enantioselective variant of this reaction is
extremely attractive, as low cost or easily accessible olefins are transformed into
highly versatile value-added enantioenriched aldehydes in a single step. However
synthetic organic chemists interested in the synthesis of fine chemicals, both in
academia and industry, have been slow to adopt this attractive protocol for the
production of chiral aldehydes. This is mainly due to the fact that in the past catalysts
for this reaction exhibited low activity and/or selectivity in this process. However, the
last two decades have seen major advances, mainly in the development of highly
effective chiral ligands, and with these developments the time has come to tackle the
vastly under-explored area of
asymmetric hydroformylation of more functionalised
olefins.
To set the scene for the research carried out during this project a brief introduction
will be given which highlights the historical development of highly efficient catalysts
for the hydroformylation of olefins. This will be accompanied by some examples of
the use of this methodology in the synthesis of pharmaceutically relevant compounds.
It should become apparent from the introduction that the
asymmetric
hydroformylation of functionalised olefins and in particular nitrogen containing
olefins, has received very little attention despite the fact that over half of all medicinal
compounds contain at least one nitrogen containing functional group.
Firstly we describe hydroformylation as a useful alternative to the classical synthesis
of a delicate chiral building block, namely α-formyl amides. These compounds,
traditionally only available through multi-step synthetic procedures from enantiopure
starting materials, have been accessed by
asymmetric hydroformylation of readily
accessible and in some cases commercially available acrylamides. By judicious
choice of reaction conditions and selection of the appropriately active chiral ligand
enantioenriched α-formyl amides (e.e. up to 82%) were produced in high yield. A
comparison is made between the classical route and the hydroformylation route to
illustrate the potential of this efficient transformation.
We have studied the hydroformylation of enamides, a much under-studied substrate
class in hydroformylation and developed knowledge of how some more
functionalised 1,1- and 1-2-subtituted olefinic amides react under…
Advisors/Committee Members: Clarke, Matt (advisor).
Subjects/Keywords: Catalysis;
Asymmetric hydroformylation;
Asymmetric synthesis;
Green chemistry
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Noonan, G. M. (2011). Asymmetric hydroformylation : a powerful tool for the synthesis of pharmaceutical intermediates
. (Thesis). University of St. Andrews. Retrieved from http://hdl.handle.net/10023/3105
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Noonan, Gary M. “Asymmetric hydroformylation : a powerful tool for the synthesis of pharmaceutical intermediates
.” 2011. Thesis, University of St. Andrews. Accessed March 04, 2021.
http://hdl.handle.net/10023/3105.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Noonan, Gary M. “Asymmetric hydroformylation : a powerful tool for the synthesis of pharmaceutical intermediates
.” 2011. Web. 04 Mar 2021.
Vancouver:
Noonan GM. Asymmetric hydroformylation : a powerful tool for the synthesis of pharmaceutical intermediates
. [Internet] [Thesis]. University of St. Andrews; 2011. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10023/3105.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Noonan GM. Asymmetric hydroformylation : a powerful tool for the synthesis of pharmaceutical intermediates
. [Thesis]. University of St. Andrews; 2011. Available from: http://hdl.handle.net/10023/3105
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of California – Berkeley
5.
Brown, Casey Jameson.
Asymmetric and Organometallic Catalysis Mediated by a Chiral Supramolecular Host.
Degree: Chemistry, 2011, University of California – Berkeley
URL: http://www.escholarship.org/uc/item/7jv7m4wh
► Chapter 1. An overview of supramolecular catalysis is presented with attention to the diverse strategies used in developing these materials. Different strategies for the design…
(more)
▼ Chapter 1. An overview of supramolecular catalysis is presented with attention to the diverse strategies used in developing these materials. Different strategies for the design and preparation of chiral supramolecular structures are described along with their applications to enantioselective binding and catalysis. The intrinsically chiral M4L612- supramolecular assembly developed by the Raymond group is introduced, and its catalytic scope is reviewed.Chapter 2. The development of an asymmetric variant of the aza-Cope transformation is presented. Application of the resolved Ga4L612- assembly to this catalytic transformation gives modest but significant enantioselectivity (up to 64% ee) with a varied scope of allyl enammonium cations. This represents the first reported example of asymmetric supramolecular catalysis with substantial enantioselectivity and catalytic turnover. Use of a relatively unreactive substrate allowed characterization of a host-substrate complex by X-ray diffraction, giving insight into the means of enantiodifferentiation by the chiral host. Additionally, the structure of the M4L612- assembly was modified by substituting other trivalent cations (Fe3+, 3+) into the M4L612- host, modulating the enantioselectivity of the rearrangement. Efforts to emulate allosteric regulation using externally associated chiral cations are also described.Chapter 3. The engineering of a high-turnover supramolecular catalyst containing a cationic ruthenium complex is described. The RuCp(PMe3)(MeCN)2+ cation, an allyl alcohol isomerization catalyst, was incorporated into the Ga4L612- assembly. While encapsulated, the organometallic complex experiences only mild rate attenuations, while maintaining its remarkably high activity. This hybrid catalyst is capable of more than 1000 turnovers, eclipsing other known supramolecular catalysts. The kinetics of catalysis are also analyzed, revealing inhibition both by acetonitrile and the allyl alcohol substrates. The protection offered by encapsulation in the assembly also allowed the preparation of the larger RuCp*(PMe3)(MeCN)2+ complex, which is both stable and catalytically active. Preliminary investigations of this complex are described.Chapter 4. Cationic gold(I) catalysts encapsulated inside assembly 1</bold are applied as supramolecular catalysts. In the presence of the Ga4L6 assembly, R3PAuX (X = Cl, Br) complexes have been found to lose their halide ligand and reside in the nanovessel's cavity as the free cation. This host-guest complex is catalytically active in both the hydroalkoxylation and hydroamination of allenes, generating cyclic, chiral ethers and amines. The rate of catalysis for the bound gold cation is observed to be higher than that for the…
Subjects/Keywords: Chemistry; asymmetric; catalysis; organometallic; supramolecular
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Brown, C. J. (2011). Asymmetric and Organometallic Catalysis Mediated by a Chiral Supramolecular Host. (Thesis). University of California – Berkeley. Retrieved from http://www.escholarship.org/uc/item/7jv7m4wh
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Brown, Casey Jameson. “Asymmetric and Organometallic Catalysis Mediated by a Chiral Supramolecular Host.” 2011. Thesis, University of California – Berkeley. Accessed March 04, 2021.
http://www.escholarship.org/uc/item/7jv7m4wh.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Brown, Casey Jameson. “Asymmetric and Organometallic Catalysis Mediated by a Chiral Supramolecular Host.” 2011. Web. 04 Mar 2021.
Vancouver:
Brown CJ. Asymmetric and Organometallic Catalysis Mediated by a Chiral Supramolecular Host. [Internet] [Thesis]. University of California – Berkeley; 2011. [cited 2021 Mar 04].
Available from: http://www.escholarship.org/uc/item/7jv7m4wh.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Brown CJ. Asymmetric and Organometallic Catalysis Mediated by a Chiral Supramolecular Host. [Thesis]. University of California – Berkeley; 2011. Available from: http://www.escholarship.org/uc/item/7jv7m4wh
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Texas A&M University
6.
Ghosh, Subrata Kumar.
The Development of New Classes of Enantioselective Hydrogen Bond Donor Catalysts for Organic Synthesis Based upon Werner Complexes.
Degree: PhD, Chemistry, 2017, Texas A&M University
URL: http://hdl.handle.net/1969.1/169551
► In this dissertation, the development of highly effective, chiral monofunctional and bifunctional hydrogen bond donor catalysts based on cobalt(III) Werner complexes and their applications in…
(more)
▼ In this dissertation, the development of highly effective, chiral monofunctional and
bifunctional hydrogen bond donor catalysts based on cobalt(III) Werner complexes and
their applications in enantioselective
catalysis have been described. Furthermore, a
protocol was developed to extend this chemistry into the fluorous media.
Section 1 provides an overview of the hydrogen bond mediated organocatalysis
and the scope of Werner complexes as hydrogen bond donors.
Section 2 describes the fundamental stereochemical features of the trication
[Co(en)3]3+ (en = ethylenediamine). Interactions between the trication, counter anions,
and solvates are analyzed and a systematic nomenclature is developed.
Section 3 provides highly diastereoselective syntheses of variety of diastereopure
salts Λ- and Δ-[Co((S,S)-NHv2CHArCHArNHv2)v3]
3+ 2X–X'– (Ar = Cv6Hv5, vCv6Hv4n-Bu, 4-
Cv6Hv4Cl, 4-Cv6Hv4CFv3, 4-Cv6Hv4OCHv3, ɑ-naphthyl, ß-naphthyl, 2-Cv6Hv4OBn; X/X' =
Cl/BArvf (BArvf = B(3,5-Cv6Hv3(CFv3)v2)v4), PFv6/BArf, BF4/BArf, PhBF3/BArf, Cl/BArf20
(BArvf20 = B(Cv6F5)4), BArf/BArf, BArf20/BArvf20, BFv4/BFv4, PFv6/PFv6) and probes their
properties.
Sections 4 and 5 provide detail applications of the lipophilic salts of Λ- or Δ-
[Co((S,S)-dpen)v3]
3+ ((S,S)-dpen = (S,S)-1,2-diphenylethylenediamine) in enantioselective
addition reactions. Under optimized conditions, Λ-[Co((S,S)-dpen)v3]
3+ 3BFv4–
catalyzes the Michael addition of dialkyl malonate to nitroalkenes in the presence of
Et3N, affording adducts in up to 98% yields and 96% ee. Interestingly, Δ-[Co((S,S)-
dpen)v3]
3+ 2Cl–BArvf20– is superior for the additions of cyclic ß-ketoesters to
azodicarboylate diesters (up to 99% yields and >99% ee).
Section 6 describes efficient syntheses of tris(hydrochloric acid) salts of chiral
triamines Hv2NCH((CHv2)nNMe2)CHv2NHv2 (n = 1-4) from commercial starting materials
in overall yields of 38-18%.
Section 7 highlights syntheses of bifunctional catalysts and their applications in
additions of dialkyl malonates to nitroalkenes. Racemic [Co(en)v2Ov2CO]
+ Cl^– and
enantiopure (S)-[Hv3NCH((CH2)nNHMe2)CHv2NHv3]
3+ 3Cl^– (n = 1-4) are combined (water/
charcoal/100 °C) to give [Co(en)v2((S)-Hv2NCH((CHv2)vnNMev2H)CHv2NHv2)]4
+ 4Cl^–.
The cobalt diastereomers (Δ/Δ)are separated via chiral Sephadex columns. Reactions
with NaOH and Na
+ BArvf^– give the catalysts Λ- or Δ-[Co(en)v2((S)-Hv2NCH-
((CHv2)nNMev2)CHv2NHv2)]
3+ 3BArvf^–. Under optimized condition, Λ-[Co(en)v2((S)-
Hv2NCH((CHv2)v3NMev2)CHv2NHv2)]
3+ 3BArvf^– gives addition products up to 98% yield and
99% ee.
Section 8 describes an optimized procedure for the synthesis of highly fluorous
Na
+ B(3,5-Cv6Hv3((CFv2)5CFv3)v2)v4– and its application in transporting polycations into
fluorous media.
Advisors/Committee Members: Gladysz, John A (advisor), Singleton, Daniel A (committee member), Darensbourg, Donald J (committee member), Tarone, Aaron M (committee member).
Subjects/Keywords: Chiral; asymmetric; catalysis; cobalt; fluorous
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Ghosh, S. K. (2017). The Development of New Classes of Enantioselective Hydrogen Bond Donor Catalysts for Organic Synthesis Based upon Werner Complexes. (Doctoral Dissertation). Texas A&M University. Retrieved from http://hdl.handle.net/1969.1/169551
Chicago Manual of Style (16th Edition):
Ghosh, Subrata Kumar. “The Development of New Classes of Enantioselective Hydrogen Bond Donor Catalysts for Organic Synthesis Based upon Werner Complexes.” 2017. Doctoral Dissertation, Texas A&M University. Accessed March 04, 2021.
http://hdl.handle.net/1969.1/169551.
MLA Handbook (7th Edition):
Ghosh, Subrata Kumar. “The Development of New Classes of Enantioselective Hydrogen Bond Donor Catalysts for Organic Synthesis Based upon Werner Complexes.” 2017. Web. 04 Mar 2021.
Vancouver:
Ghosh SK. The Development of New Classes of Enantioselective Hydrogen Bond Donor Catalysts for Organic Synthesis Based upon Werner Complexes. [Internet] [Doctoral dissertation]. Texas A&M University; 2017. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/1969.1/169551.
Council of Science Editors:
Ghosh SK. The Development of New Classes of Enantioselective Hydrogen Bond Donor Catalysts for Organic Synthesis Based upon Werner Complexes. [Doctoral Dissertation]. Texas A&M University; 2017. Available from: http://hdl.handle.net/1969.1/169551

Colorado State University
7.
White, Nicholas Andrew.
Enantioselective β-functionalization of enals via N-heterocyclic carbene catalysis.
Degree: PhD, Chemistry, 2015, Colorado State University
URL: http://hdl.handle.net/10217/170358
► A series of δ-nitroesters were synthesized through the N-heterocyclic carbene catalyzed coupling of enals and nitroalkenes. The asymmetric coupling of these substrates via the homoenolate…
(more)
▼ A series of δ-nitroesters were synthesized through the N-heterocyclic carbene catalyzed coupling of enals and nitroalkenes. The
asymmetric coupling of these substrates via the homoenolate pathway afford δ-nitroesters in good yield, diastereoselectivity, and enantioselectivity. This methodology allows for the rapid synthesis of δ-lactams. Using this approach, we synthesized the pharmaceutically relevant piperidines paroxetine and femoxetine. A novel single-electron oxidation pathway for the N-heterocyclic carbene generated Breslow intermediate has been developed. Nitroarenes have been shown to transfer an oxygen from the nitro group to the β-position of an enal in an
asymmetric fashion to generate β-hydroxy esters. This reaction affords desired β-hydroxy ester products in good yield and enantioselectivity and tolerates a wide range of enal substrates. A dimerization of aromatic enals to form 3,4-disubstituted cyclopentanones has been investigated. Using a single-electron oxidant, aromatic enals couple to form cyclopenanone products in good yield, good enantioselectivity, and excellent diastereoselectivity. A cross coupling has also been developed to afford non-symmetrical cyclopentanone products.
Advisors/Committee Members: Rovis, Tomislav (advisor), Kennan, Alan J. (committee member), Chen, Eugene Y.-X. (committee member), Williams, Robert M. (committee member), Kipper, Matt J. (committee member).
Subjects/Keywords: asymmetric; carbene; catalysis; organic
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APA (6th Edition):
White, N. A. (2015). Enantioselective β-functionalization of enals via N-heterocyclic carbene catalysis. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/170358
Chicago Manual of Style (16th Edition):
White, Nicholas Andrew. “Enantioselective β-functionalization of enals via N-heterocyclic carbene catalysis.” 2015. Doctoral Dissertation, Colorado State University. Accessed March 04, 2021.
http://hdl.handle.net/10217/170358.
MLA Handbook (7th Edition):
White, Nicholas Andrew. “Enantioselective β-functionalization of enals via N-heterocyclic carbene catalysis.” 2015. Web. 04 Mar 2021.
Vancouver:
White NA. Enantioselective β-functionalization of enals via N-heterocyclic carbene catalysis. [Internet] [Doctoral dissertation]. Colorado State University; 2015. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10217/170358.
Council of Science Editors:
White NA. Enantioselective β-functionalization of enals via N-heterocyclic carbene catalysis. [Doctoral Dissertation]. Colorado State University; 2015. Available from: http://hdl.handle.net/10217/170358

Rice University
8.
Sambasivan, Ramya.
Rh(II) metallopeptides for asymmetric catalysis.
Degree: PhD, Natural Sciences, 2015, Rice University
URL: http://hdl.handle.net/1911/95526
► The development of peptides as chiral ligands for asymmetric Rh(II) catalysis is discussed in this work. Mother Nature’s solution to chiral ligand design is to…
(more)
▼ The development of peptides as chiral ligands for
asymmetric Rh(II)
catalysis is discussed in this work. Mother Nature’s solution to chiral ligand design is to make use of the naturally available chiral building blocks – amino acids. Polypeptides, built from amino acids, provide a diverse, modular and functional-group-rich framework for the development of selective transition- metal catalysts and enable facile ligand screening.
The dirhodium core has a paddlewheel structure that can ligate readily to the side chain carboxylate of aspartate or glutamate in a peptide chain. When a peptide containing aspartates or glutamates in the i and i+4 position is complexed to dirhodium, the transition metal complex thus formed has a defined peptide secondary structure with retention of catalytic activity at the metal center.
The first-generation approach used a solution-phase library of dirhodium bis-peptide catalysts for the enantioselective Si–H bond insertion and cyclopropanation. The parallel and anti-parallel orientation of bis-peptide catalysts was determined by pyrene fluorescence. Subsequently, parallel on-bead screening of catalyst libraries allowed significantly higher throughput by obviating the need for purification and isolation of individual catalysts. This enables the synthesis and screening of catalysts in 96-well plate format within a few days. More recently, a mono-peptide catalyst with a tridentate eq-eq-ax peptide ligand has been identified which exhibits differential behavior in solution and on bead. New insights into the development of immobilized homogeneous catalysts for stereoselective
catalysis are discussed.
Advisors/Committee Members: Ball, Zachary T. (advisor), Engel, Paul S. (advisor), Verduzco, Rafael (committee member).
Subjects/Keywords: metallopeptide; asymmetric catalysis; rhodium catalyst
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Sambasivan, R. (2015). Rh(II) metallopeptides for asymmetric catalysis. (Doctoral Dissertation). Rice University. Retrieved from http://hdl.handle.net/1911/95526
Chicago Manual of Style (16th Edition):
Sambasivan, Ramya. “Rh(II) metallopeptides for asymmetric catalysis.” 2015. Doctoral Dissertation, Rice University. Accessed March 04, 2021.
http://hdl.handle.net/1911/95526.
MLA Handbook (7th Edition):
Sambasivan, Ramya. “Rh(II) metallopeptides for asymmetric catalysis.” 2015. Web. 04 Mar 2021.
Vancouver:
Sambasivan R. Rh(II) metallopeptides for asymmetric catalysis. [Internet] [Doctoral dissertation]. Rice University; 2015. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/1911/95526.
Council of Science Editors:
Sambasivan R. Rh(II) metallopeptides for asymmetric catalysis. [Doctoral Dissertation]. Rice University; 2015. Available from: http://hdl.handle.net/1911/95526
9.
Minerali, Eni.
Asymmetric synthesis of enantioenriched spirocycles via a chiral Brønsted acid catalyzed desymmetrization.
Degree: 2019, NC Docks
URL: http://libres.uncg.edu/ir/uncg/f/Minerali_uncg_0154M_12848.pdf
► Asymmetric methodologies are very important as they allow chemists to produce significant quantities of complex chiral molecules as enantiopure or enantioenriched compounds. The Petersen group…
(more)
▼ Asymmetric methodologies are very important as they allow chemists to produce significant quantities of complex chiral molecules as enantiopure or enantioenriched compounds. The Petersen group has previously developed chiral Brønsted acid catalyzed desymmetrization reactions for the asymmetric synthesis of lactones. The work described in this thesis provides an application for this methodology to the synthesis of enantioenriched spirocycles, motifs present in many biologically active molecules. This synthesis is performed in the presence of TRIP, a chiral BINOL-derived phosphoric acid catalyst, which guides the cyclization of symmetric prochiral intermediates. The research in this thesis describes the synthesis of two enantioenriched spirocycles, one of which posed many synthetic challenges. Even though the results were nonconclusive, more synthetic work towards the understanding of the mechanistic pathway is also introduced. Therefore, the work described herein not only contributes to the substrate scope of the reaction that was developed, but also provides discussion to the challenges faced during the synthesis of these compounds.
Subjects/Keywords: Asymmetric synthesis; Chirality; Catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Minerali, E. (2019). Asymmetric synthesis of enantioenriched spirocycles via a chiral Brønsted acid catalyzed desymmetrization. (Thesis). NC Docks. Retrieved from http://libres.uncg.edu/ir/uncg/f/Minerali_uncg_0154M_12848.pdf
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Minerali, Eni. “Asymmetric synthesis of enantioenriched spirocycles via a chiral Brønsted acid catalyzed desymmetrization.” 2019. Thesis, NC Docks. Accessed March 04, 2021.
http://libres.uncg.edu/ir/uncg/f/Minerali_uncg_0154M_12848.pdf.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Minerali, Eni. “Asymmetric synthesis of enantioenriched spirocycles via a chiral Brønsted acid catalyzed desymmetrization.” 2019. Web. 04 Mar 2021.
Vancouver:
Minerali E. Asymmetric synthesis of enantioenriched spirocycles via a chiral Brønsted acid catalyzed desymmetrization. [Internet] [Thesis]. NC Docks; 2019. [cited 2021 Mar 04].
Available from: http://libres.uncg.edu/ir/uncg/f/Minerali_uncg_0154M_12848.pdf.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Minerali E. Asymmetric synthesis of enantioenriched spirocycles via a chiral Brønsted acid catalyzed desymmetrization. [Thesis]. NC Docks; 2019. Available from: http://libres.uncg.edu/ir/uncg/f/Minerali_uncg_0154M_12848.pdf
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Colorado State University
10.
Vora, Harit.
N-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids.
Degree: PhD, Chemistry, 2011, Colorado State University
URL: http://hdl.handle.net/10217/52114
► N-heterocyclic carbene catalyzed α-redox reaction has been utilized towards the catalytic synthesis of amides utilizing amines and substoichiometric quantities of an acyl transfer reagent in…
(more)
▼ N-heterocyclic carbene catalyzed α-redox reaction has been utilized towards the catalytic synthesis of amides utilizing amines and substoichiometric quantities of an acyl transfer reagent in a waste reduced acylation process. The reaction is amenable to a plethora of amines and amine hydrochloride salts as nucleophiles. The reaction is applicable towards a variety α-reducible aldehydes as α,α-dichloro aldehydes, enals, epoxy and aziridnyl aldehydes all provide the respective amides in moderate to excellent yields with the latter in high diastereoselectivity. The
asymmetric amidation reaction provides chiral amides in moderate enantioselectivity. Additionally, the N-heterocyclic carbene catalyzed α-redox reaction was also utilized for the synthesis of enantioenriched α-chloro and α-fluoro carboxylic acids. The reaction also provide for a mild installation of a deuterium from D2O furnishing enantioenriched isotopically labeled compounds. Investigations in to the mechanism have revealed that the carbene displays behavior of a phase transfer reagent by shuttling hydroxide from the aqueous phase to the organic phase. Additionally, it has been found that the turnover limiting step in this acylation process in the hydrolysis of the acyl azolium.
Advisors/Committee Members: Rovis, Tomislav (advisor), Williams, Robert (committee member), Wood, John (committee member), Chen, Eugene (committee member), McNeil, Michael (committee member).
Subjects/Keywords: synthesis; NHC catalysis; organic chemistry; asymmetric; catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Vora, H. (2011). N-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/52114
Chicago Manual of Style (16th Edition):
Vora, Harit. “N-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids.” 2011. Doctoral Dissertation, Colorado State University. Accessed March 04, 2021.
http://hdl.handle.net/10217/52114.
MLA Handbook (7th Edition):
Vora, Harit. “N-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids.” 2011. Web. 04 Mar 2021.
Vancouver:
Vora H. N-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids. [Internet] [Doctoral dissertation]. Colorado State University; 2011. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10217/52114.
Council of Science Editors:
Vora H. N-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids. [Doctoral Dissertation]. Colorado State University; 2011. Available from: http://hdl.handle.net/10217/52114
11.
Stache, Erin Elizabeth.
Dual nickel- and photoredox-catalyzed enantioselective desymmetrization of meso anhydrides and C-O bond activation via phosphines and photoredox catalysis.
Degree: PhD, Chemistry, 2018, Colorado State University
URL: http://hdl.handle.net/10217/191328
► Described herein is the application of photoredox catalysis in the development of new synthetic methods. A dual nickel- and photoredox catalyzed desymmetrization of meso succinic…
(more)
▼ Described herein is the application of photoredox
catalysis in the development of new synthetic methods. A dual nickel- and photoredox catalyzed desymmetrization of meso succinic anhydrides was developed to generate stereodefined cis keto-acids in high enantioselectivity and diastereoselectivity. The approach employed benzylic radicals as a coupling partner, generated from a photoredox catalyzed single-electron oxidation of benzylic trifluoroborates using an inexpensive organic dye. A unique epimerization event was discovered and the degree of epimerization was rendered tunable by changing catalyst loadings to ultimately form the trans diastereomer preferentially in high enantioeselectivity. A method for the C–O bond activation of aliphatic alcohols and carboxylic acids was developed using phosphines and photoredox
catalysis. This novel reaction platform was used to generate aliphatic or acyl radicals directly from benzylic alcohols and aliphatic and aromatic acids, and with terminal hydrogen atom transfer, afforded the desired deoxygenated alkanes and aldehydes. Additionally, the intermediate acyl radicals could be intercepted in an intramolecular cyclization reaction to generate new lactones, amides and ketones.
Advisors/Committee Members: Rovis, Tomislav (advisor), Doyle, Abigail G. (advisor), Chen, Eugene (committee member), McNally, Andy (committee member), Reynolds, Melissa (committee member), Kipper, Matt (committee member).
Subjects/Keywords: nickel catalysis; photochemistry; organic synthesis; asymmetric catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Stache, E. E. (2018). Dual nickel- and photoredox-catalyzed enantioselective desymmetrization of meso anhydrides and C-O bond activation via phosphines and photoredox catalysis. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/191328
Chicago Manual of Style (16th Edition):
Stache, Erin Elizabeth. “Dual nickel- and photoredox-catalyzed enantioselective desymmetrization of meso anhydrides and C-O bond activation via phosphines and photoredox catalysis.” 2018. Doctoral Dissertation, Colorado State University. Accessed March 04, 2021.
http://hdl.handle.net/10217/191328.
MLA Handbook (7th Edition):
Stache, Erin Elizabeth. “Dual nickel- and photoredox-catalyzed enantioselective desymmetrization of meso anhydrides and C-O bond activation via phosphines and photoredox catalysis.” 2018. Web. 04 Mar 2021.
Vancouver:
Stache EE. Dual nickel- and photoredox-catalyzed enantioselective desymmetrization of meso anhydrides and C-O bond activation via phosphines and photoredox catalysis. [Internet] [Doctoral dissertation]. Colorado State University; 2018. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10217/191328.
Council of Science Editors:
Stache EE. Dual nickel- and photoredox-catalyzed enantioselective desymmetrization of meso anhydrides and C-O bond activation via phosphines and photoredox catalysis. [Doctoral Dissertation]. Colorado State University; 2018. Available from: http://hdl.handle.net/10217/191328

University of St. Andrews
12.
Durrani, Jamie T.
Palladium catalysed asymmetric hydroxy- and alkoxycarbonylation of alkenes
.
Degree: 2015, University of St. Andrews
URL: http://hdl.handle.net/10023/6276
► Palladium catalysed asymmetric hydroxy- and alkoxycarbonylation reactions of alkenes have the potential to deliver valuable chiral carboxylic acid and ester building blocks from cheap feedstocks:…
(more)
▼ Palladium catalysed
asymmetric hydroxy- and alkoxycarbonylation reactions of alkenes have the potential to deliver valuable chiral carboxylic acid and ester building blocks from cheap feedstocks: alkenes, carbon monoxide and water (alcohols in the case of alkoxycarbonylation). Despite the attractive nature of these reactions, extensive research has so far been unable to produce effective catalysts which are capable of controlling both regio- and enantioselectivity.
Building on exciting recent results involving the use of highly enantioselective palladium catalysts derived from Phanephos-type ligands, this research focuses on paracyclophane-diphosphines and their use in
asymmetric hydroxy- and alkoxycarbonylation reactions.
An investigation into reaction conditions analysed several factors, including solvents, CO-pressure, acidic additives and halide sources, to provide optimal activity and selectivities. Two novel electron-poor paracyclophane-diphosphines and their mono- and di-palladium complexes were synthesised and shown to provide exceptional levels of regioselectivity while maintaining high levels of
asymmetric induction. These are the first such examples of hydroxy- or alkoxycarbonylation catalysts to facilitate simultaneous control over both regio- and enantioselectivity. The most effective catalyst was used to promote the reactions of a selection of aryl alkenes and was shown to be tolerant of several different functional groups. A selection of non-symmetric paracyclophane-diphosphine ligands and their palladium complexes were also synthesised and assessed for their performance in hydroxy- and alkoxycarbonylation. We also report the use of Phanephos-type ligands to promote the highly enantioselective hydroxycarbonylation of N-(p-toluenesulfonyl)-3-pyrroline to deliver a chiral proline derivative in high ee.
Advisors/Committee Members: Clarke, Matt (advisor).
Subjects/Keywords: Hydroxycarbonylation;
Alkoxycarbonylation;
Carbonylation;
Asymmetric catalysis;
Homogeneous catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Durrani, J. T. (2015). Palladium catalysed asymmetric hydroxy- and alkoxycarbonylation of alkenes
. (Thesis). University of St. Andrews. Retrieved from http://hdl.handle.net/10023/6276
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Durrani, Jamie T. “Palladium catalysed asymmetric hydroxy- and alkoxycarbonylation of alkenes
.” 2015. Thesis, University of St. Andrews. Accessed March 04, 2021.
http://hdl.handle.net/10023/6276.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Durrani, Jamie T. “Palladium catalysed asymmetric hydroxy- and alkoxycarbonylation of alkenes
.” 2015. Web. 04 Mar 2021.
Vancouver:
Durrani JT. Palladium catalysed asymmetric hydroxy- and alkoxycarbonylation of alkenes
. [Internet] [Thesis]. University of St. Andrews; 2015. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10023/6276.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Durrani JT. Palladium catalysed asymmetric hydroxy- and alkoxycarbonylation of alkenes
. [Thesis]. University of St. Andrews; 2015. Available from: http://hdl.handle.net/10023/6276
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Université Catholique de Louvain
13.
Nahra, Fady.
Study of new reactions catalysed by copper(I) complexes : investigation of domino catalysis- and dual catalysis-type reactions.
Degree: 2013, Université Catholique de Louvain
URL: http://hdl.handle.net/2078.1/133426
► In this thesis we are going to first discuss the application of a copper hydride system, which was previously developed in our lab, to new…
(more)
▼ In this thesis we are going to first discuss the application of a copper hydride system, which was previously developed in our lab, to new Michael acceptors bearing a nitrogen group on the double bond. We are equally going to illustrate the development of a new cooperative dual catalysis strategy based on a CuI/Pd0 system. This strategy allowed us to successfully access α-allylated ketones diastereoselectively as well as enantioselectively.
In a later point, we are also going to examine the development of two synthetic pathways to generate unprecedented (NHC)CuI bifluoride complexes. We tested the activity of these complexes in several known CuI-catalyzed reactions, and consequently established the first CuI-catalyzed diastereoselective allylation of (R)-N-tert-butanesulfinyl aldimines. The method enables efficient, simple and general synthesis of enantiomerically enriched homoallylic amines at room temperature in high yields.
(CHIM 3) – UCL, 2013
Advisors/Committee Members: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity, Riant, Olivier, Gohy, Jean-François, Elias, Benjamin, Poli, Giovanni, Gagosz, Fabien, Van Der Eycken, Johan.
Subjects/Keywords: Asymmetric catalysis; Copper(I); Palladium(0); Domino catalysis; Dual catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Nahra, F. (2013). Study of new reactions catalysed by copper(I) complexes : investigation of domino catalysis- and dual catalysis-type reactions. (Thesis). Université Catholique de Louvain. Retrieved from http://hdl.handle.net/2078.1/133426
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Nahra, Fady. “Study of new reactions catalysed by copper(I) complexes : investigation of domino catalysis- and dual catalysis-type reactions.” 2013. Thesis, Université Catholique de Louvain. Accessed March 04, 2021.
http://hdl.handle.net/2078.1/133426.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Nahra, Fady. “Study of new reactions catalysed by copper(I) complexes : investigation of domino catalysis- and dual catalysis-type reactions.” 2013. Web. 04 Mar 2021.
Vancouver:
Nahra F. Study of new reactions catalysed by copper(I) complexes : investigation of domino catalysis- and dual catalysis-type reactions. [Internet] [Thesis]. Université Catholique de Louvain; 2013. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/2078.1/133426.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Nahra F. Study of new reactions catalysed by copper(I) complexes : investigation of domino catalysis- and dual catalysis-type reactions. [Thesis]. Université Catholique de Louvain; 2013. Available from: http://hdl.handle.net/2078.1/133426
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of St. Andrews
14.
Gilbert, Sophie Hannah.
Rhodium catalysed asymmetric synthesis of tertiary amines
.
Degree: 2020, University of St. Andrews
URL: http://hdl.handle.net/10023/19528
► The asymmetric synthesis of tertiary amines is a highly desirable goal, but far fewer efficient synthetic methods exist for their synthesis, relative to primary and…
(more)
▼ The
asymmetric synthesis of tertiary amines is a highly desirable goal, but far fewer efficient
synthetic methods exist for their synthesis, relative to primary and secondary amines. A
possible atom-efficient method of tertiary amine formation is catalytic hydrogenation.
Despite the demand, there are only a few reported examples of
asymmetric enamine
hydrogenation, and none of these conditions are efficient enough to be viable for industrial
processes. Until 2019, there were no reported examples of tertiary amine formation by using
direct
asymmetric reductive amination using H₂ as the reductant.
This thesis describes the development of both enantioselective and diastereoselective
reductive aminations, using hydrogen gas and homogeneous rhodium catalysts. The
enantioselective reductive amination uses an electron deficient phanephos ligand and
reduces bicyclic aryl ketones at low catalyst loadings but moderate selectivity. The
diastereoselective reductive amination uses electron deficient monophosphines as ligands
and includes many chiral 3-substituted cyclic ketones in the substrate scope, mainly 3-
arylcyclohexanones.
These 3-arylcyclohexanones substrates were synthesised by rhodium catalysed conjugate
addition. This enantioselective conjugate addition was combined with our diastereoselective
reductive amination, to form a highly stereoselective one-pot process. The rhodium used in
the conjugate addition was recycled for the reductive amination step using an ‘assisted
tandem catalysis’ strategy. The rhodium catalyst was modified in situ by the sequential
addition of a monophosphine ligand, allowing it to catalyse the second step. This process
formed a chiral tertiary amine with high selectivity and conversion.
While developing this one-pot process, BOBPHOS, a phospholane-phosphite ligand, was
identified as a highly active ligand in rhodium catalysed conjugate additions. The potential
of BOBPHOS-Rh catalysed conjugate additions of challenging substrates like piperidones,
coumarins and heteroarylboronic acids was examined, leading to improved protocols.
Advisors/Committee Members: Clarke, Matt (advisor).
Subjects/Keywords: Chemistry;
Catalysis;
Homogeneous catalysis;
Hydrogenation;
Asymmetric catalysis;
Chiral amines;
Organometallic chemistry
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Gilbert, S. H. (2020). Rhodium catalysed asymmetric synthesis of tertiary amines
. (Thesis). University of St. Andrews. Retrieved from http://hdl.handle.net/10023/19528
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Gilbert, Sophie Hannah. “Rhodium catalysed asymmetric synthesis of tertiary amines
.” 2020. Thesis, University of St. Andrews. Accessed March 04, 2021.
http://hdl.handle.net/10023/19528.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Gilbert, Sophie Hannah. “Rhodium catalysed asymmetric synthesis of tertiary amines
.” 2020. Web. 04 Mar 2021.
Vancouver:
Gilbert SH. Rhodium catalysed asymmetric synthesis of tertiary amines
. [Internet] [Thesis]. University of St. Andrews; 2020. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10023/19528.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Gilbert SH. Rhodium catalysed asymmetric synthesis of tertiary amines
. [Thesis]. University of St. Andrews; 2020. Available from: http://hdl.handle.net/10023/19528
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of California – Berkeley
15.
Neel, Andrew James.
Toward the Rational Design of Asymmetric Catalysts using Attractive Non-Covalent Interactions and Design Elements.
Degree: Chemistry, 2016, University of California – Berkeley
URL: http://www.escholarship.org/uc/item/34d2396n
► Throughout my doctoral studies, I have endeavored to address the question of how to rationally design chiral catalysts to control enantioselectivity in a predictable fashion.…
(more)
▼ Throughout my doctoral studies, I have endeavored to address the question of how to rationally design chiral catalysts to control enantioselectivity in a predictable fashion. To approach this problem, I have focused on the strategic implementation of attractive non-covalent interactions between catalysts and their substrates at the enantiodetermining transition state. A significant portion of this work involved the development of an approach to elucidating the structural origins of selectivity in complex data sets, with an eye towards rational catalyst design. The insights gained from these studies constitute the subject matter of this dissertation.Chapter 1 provides an overview of a subset of attractive non-covalent interactions involving aromatic rings. Examples are highlighted in which these interactions have been characterized in the ground state with the explicit intention of quantifying their strengths and geometric requirements. Using the lessons learned from these reports, case studies are presented in which the interactions under discussion have been leveraged to catalyze chemical reactions via the paradigm of transition state stabilization. The insight gleaned from this literature survey is intended to provide a framework for the discussion of the catalyst design concepts outlined in the following chapters.Chapter 2 describes the development of a novel class of axially chiral triazole containing phosphoric acid catalysts designed to impart enantioselectivity via attractive non-covalent interactions with a substrate at the enantiodetermining TS. This strategy stands in contrast to that typically discussed in the literature in which catalyst steric bulk is frequently invoked to rationalize asymmetric induction. Using this newly prepared catalyst library, an enantioselective cross dehydrogenative coupling was developed within the conceptual framework of the Toste group’s strategy of chiral anion phase transfer catalysis. Preliminary experiments suggested that the triazole substituents played a role in the determination of asymmetric induction beyond steric bulk, as initially hypothesized. The third chapter describes our efforts to elucidate the structural origins of enantioselectivity in the oxidative coupling reaction presented in Chapter 2. By obtaining an enantioselectivity data set based on strategically modulated catalysts and substrates, we applied linear regression techniques to correlate our experimental data with molecular descriptors describing the structural variation throughout the data set. The resulting models, along with the overall enantioselectivity trends, were used to develop intuitively sensible mechanistic hypotheses that were subsequently tested through the application of new catalysts specifically tailored to address them. Based on the hypothesis that the triazole catalysts were engaged in enantiodetermining interactions with the substrates at the TS, we rationally designed catalysts that afforded the products with the highest enantiomeric excesses reported to…
Subjects/Keywords: Chemistry; Asymmetric Catalysis; Organic Synthesis; Organocatalysis
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APA ·
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APA (6th Edition):
Neel, A. J. (2016). Toward the Rational Design of Asymmetric Catalysts using Attractive Non-Covalent Interactions and Design Elements. (Thesis). University of California – Berkeley. Retrieved from http://www.escholarship.org/uc/item/34d2396n
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Neel, Andrew James. “Toward the Rational Design of Asymmetric Catalysts using Attractive Non-Covalent Interactions and Design Elements.” 2016. Thesis, University of California – Berkeley. Accessed March 04, 2021.
http://www.escholarship.org/uc/item/34d2396n.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Neel, Andrew James. “Toward the Rational Design of Asymmetric Catalysts using Attractive Non-Covalent Interactions and Design Elements.” 2016. Web. 04 Mar 2021.
Vancouver:
Neel AJ. Toward the Rational Design of Asymmetric Catalysts using Attractive Non-Covalent Interactions and Design Elements. [Internet] [Thesis]. University of California – Berkeley; 2016. [cited 2021 Mar 04].
Available from: http://www.escholarship.org/uc/item/34d2396n.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Neel AJ. Toward the Rational Design of Asymmetric Catalysts using Attractive Non-Covalent Interactions and Design Elements. [Thesis]. University of California – Berkeley; 2016. Available from: http://www.escholarship.org/uc/item/34d2396n
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Mississippi State University
16.
Chakraborty, Amarraj.
The method development for synthesizing chiral CCC-NHC Zr pincer complexes.
Degree: MS, Chemistry, 2015, Mississippi State University
URL: http://sun.library.msstate.edu/ETD-db/theses/available/etd-08062015-162047/
;
► There are numerous classes of N-heterocyclic carbenes (NHCs) that have been synthesized since the discovery of stable NHCs in 1988. Their application as ligands…
(more)
▼ There are numerous classes of N-heterocyclic carbenes (NHCs) that have been synthesized since the discovery of stable NHCs in 1988. Their application as ligands in metal complexes has received much attention because of their strong sigma-donor and poor pi-acceptor properties. Within these NHC metal complexes, we are interested in studying zirconium metal complexes with pincer NHC ligands. Recently, achiral CCC-NHC pincer zirconium complexes were synthesized and their catalytic activity in intramolecular hydroamination of aminoalkenes were reported.
Herein is reported new reaction conditions which yield pure, chiral CCC-NHC Zr pincer mono(amido) dibromo complex. The enantiopure crystal structure of the same complex is reported. Attempts to synthesize chiral CCC-NHC Zr pincer bis- and tris- amido complexes with the iodo salt of the ligand precursor are summarized. Moreover, syntheses of chiral bis(imidazolinium) ligand precursors with different counter anions are reported with optimized reaction conditions.
Advisors/Committee Members: Keith T. Mead (chair), Andrzej Sygula (committee member), Joseph Emerson (committee member).
Subjects/Keywords: synthesis; Zr chemistry; organometallic chemistry; asymmetric catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Chakraborty, A. (2015). The method development for synthesizing chiral CCC-NHC Zr pincer complexes. (Masters Thesis). Mississippi State University. Retrieved from http://sun.library.msstate.edu/ETD-db/theses/available/etd-08062015-162047/ ;
Chicago Manual of Style (16th Edition):
Chakraborty, Amarraj. “The method development for synthesizing chiral CCC-NHC Zr pincer complexes.” 2015. Masters Thesis, Mississippi State University. Accessed March 04, 2021.
http://sun.library.msstate.edu/ETD-db/theses/available/etd-08062015-162047/ ;.
MLA Handbook (7th Edition):
Chakraborty, Amarraj. “The method development for synthesizing chiral CCC-NHC Zr pincer complexes.” 2015. Web. 04 Mar 2021.
Vancouver:
Chakraborty A. The method development for synthesizing chiral CCC-NHC Zr pincer complexes. [Internet] [Masters thesis]. Mississippi State University; 2015. [cited 2021 Mar 04].
Available from: http://sun.library.msstate.edu/ETD-db/theses/available/etd-08062015-162047/ ;.
Council of Science Editors:
Chakraborty A. The method development for synthesizing chiral CCC-NHC Zr pincer complexes. [Masters Thesis]. Mississippi State University; 2015. Available from: http://sun.library.msstate.edu/ETD-db/theses/available/etd-08062015-162047/ ;

University of Alberta
17.
Rauniyar, Vivek.
Mechanistic Investigation, Development and Synthetic
Applications of a Catalytic Enantioselective and Diastereoselective
Allylboration Methodology.
Degree: PhD, Department of Chemistry, 2009, University of Alberta
URL: https://era.library.ualberta.ca/files/kw52j8708
► Over the past two decades and continuing on, carbonyl allylation chemistry has been a very useful and popular tool for the stereocontrolled formation of carbon-carbon…
(more)
▼ Over the past two decades and continuing on, carbonyl
allylation chemistry has been a very useful and popular tool for
the stereocontrolled formation of carbon-carbon bonds in the field
of organic synthesis. In the context of natural product synthesis,
the efficiency and status of aldehyde allylboration method is only
matched by the asymmetric and diastereoselective aldol methodology.
Unfortunately, prior to the new millennium, the means to control
the absolute stereoselectivity in the addition of allylic boron
reagents had been restricted to stoichiometric chiral directors,
appended onto the metal center. In 2002, the research groups of
Hall and Miyaura reported a new Lewis acid-catalyzed allylboration
reaction manifold, which raised intriguing mechanistic questions
and also paved the way for a catalytic enantioselective methodology
development. Chapter 2 of this thesis details mechanistic studies
related to the new Lewis acid-catalyzed allylboration. In this
chapter, various control experiments and kinetic studies are
presented, the results of which allowed us to propose a hypothesis
involving the electrophilic boronate activation as the key factor
for the observed rate enhancement. Chapter 3 describes the initial
phase of our research to develop a catalytic enantioselective
allylboration methodology. We discovered that Brønsted acid
catalysts derived from diol•SnCl4 complexes were promising
catalysts for the asymmetric addition of air and moisture stable
and commercially available allylic pinacol boronates. Under this
1st generation catalyst-system, the corresponding homoallylic
alcohols were obtained in moderate to good enantioselectivity and
excellent diastereoselectivity. The development of a novel chiral
Brønsted acid catalyst for the highly enantio- and
diastereoselective allylboration reaction methodology is the single
most important result to come from this thesis. Chapter 4 outlines
the development of the 2nd generation catalyst system. A systematic
study of the diol component of the catalyst system led us to arrive
at a novel diol nicknamed Vivol on behalf of my contribution. The
resulting Brønsted acid derived from Vivol•SnCl4 now provided the
corresponding homoallylic alcohol products in very good to
excellent enantioselectivity. Preliminary mechanistic studies along
with the X-ray diffraction structure of the catalyst system are
also presented. Based on this information, an even better
performaning diol (termed F-Vivol) was developed. This 3rd
generation catalyst system derived from F-Vivol•SnCl4 complex was
shown to display consistently superior reactivity and selectivity
over its 2nd generation predecessor. Chapter 5 describes our
efforts to expand the reagent scope of the Brønsted acid catalyzed
allylboration methodology. Furthermore, this chapter also describes
the successful application of the catalytic process towards the
synthesis of simple and complex molecules. Accordingly, the
preparation and application of the Brønsted acid-catalyzed addition
of 2-bromoallyl boron pinacolate is described.…
Subjects/Keywords: Asymmetric Catalysis, Allylboration, Allylboronate,
Palmerolide A
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Rauniyar, V. (2009). Mechanistic Investigation, Development and Synthetic
Applications of a Catalytic Enantioselective and Diastereoselective
Allylboration Methodology. (Doctoral Dissertation). University of Alberta. Retrieved from https://era.library.ualberta.ca/files/kw52j8708
Chicago Manual of Style (16th Edition):
Rauniyar, Vivek. “Mechanistic Investigation, Development and Synthetic
Applications of a Catalytic Enantioselective and Diastereoselective
Allylboration Methodology.” 2009. Doctoral Dissertation, University of Alberta. Accessed March 04, 2021.
https://era.library.ualberta.ca/files/kw52j8708.
MLA Handbook (7th Edition):
Rauniyar, Vivek. “Mechanistic Investigation, Development and Synthetic
Applications of a Catalytic Enantioselective and Diastereoselective
Allylboration Methodology.” 2009. Web. 04 Mar 2021.
Vancouver:
Rauniyar V. Mechanistic Investigation, Development and Synthetic
Applications of a Catalytic Enantioselective and Diastereoselective
Allylboration Methodology. [Internet] [Doctoral dissertation]. University of Alberta; 2009. [cited 2021 Mar 04].
Available from: https://era.library.ualberta.ca/files/kw52j8708.
Council of Science Editors:
Rauniyar V. Mechanistic Investigation, Development and Synthetic
Applications of a Catalytic Enantioselective and Diastereoselective
Allylboration Methodology. [Doctoral Dissertation]. University of Alberta; 2009. Available from: https://era.library.ualberta.ca/files/kw52j8708

Penn State University
18.
Li, Wei.
Design and Synthesis of Chiral Ligands and Their Applications in Transition Metal-catalyzed Asymmetric Reactions.
Degree: 2012, Penn State University
URL: https://submit-etda.libraries.psu.edu/catalog/12770
► Transition metal catalyzed reactions are among the most powerful and direct approaches for the synthesis of organic molecules. During the past several decades, phosphorous-containing ligands…
(more)
▼ Transition metal catalyzed reactions are among the most powerful and direct approaches for the synthesis of organic molecules. During the past several decades, phosphorous-containing ligands have been extensively studied in transition metal -catalyzed transformations particularly
asymmetric hydrogenations. Development of new chiral ligands and efficient catalyst systems for various prochiral unsaturated substrates in
asymmetric hydrogenations are the focus of this dissertation. An important family of atropisomeric biaryl bisphosphine ligands, C3*-TunePhos and related bisaminophosphines have been designed and synthesized. The Ru catalysts of the highly modular C3*-TunePhos have been proved to be highly efficient (up to 99.8% ee, up to 1,000,000 TON) for practical
asymmetric hydrogenations of a wide range of unfunctionalized ketones as well as α-, β- keto esters and N-2-substituted allylphthalimides. The synthetic utility of bisaminophosphine ligands was studied for rhodium-catalyzed
asymmetric hydrogenations of α-dehydroamino acid esters, affording up to 98% ee’s. A new chiral tridentate NNN-type indan-Ambox ligand was designed and synthesized targeting the direct hydrogenation of unfunctionalized aryl and alkyl ketones. Successful examples of unfunctionalized ketone reduction in a enantioselective catalytic pathway display the potential of tridentate ligands in
asymmetric catalysis. Another rational design and synthesis of PNP-type bulky chiral tridentate ligand was also fulfilled, yet it failed to provide superior enantioselectivity. To solve the problems of
asymmetric hydrogenation of imines and heteroaromatics, a series of Ir- or Pd-based catalyst systems have been developed. Highly enantioselective and highly efficient hydrogenation of N-aryl imine, N-H imines, β-enamine esters, quinoline derivatives and unprotected indole derivatives have been successfully achieved respectively, with up to 98% ee and 10,000 TON. Catalyst systems containing strongly electron-donating and sterically hindered bisphosphine ligand have displayed significant advantages and will lead to more updated breakthroughs. Other examples of transition metal-catalyzed reactions such as Cu-catalyzed conjugate reduction of cyclic α,β-unsaturated ketones and Ru-catalyzed dynamic kinetic resolution of α-substituted cyclic ketones have also been investigated. Some preliminary results were discussed accordingly.
Advisors/Committee Members: Dr Gong Chen, Dissertation Advisor/Co-Advisor, Dr Tom Mallouk, Committee Member, Alexander Thomas Radosevich, Committee Member, Dr Qing Wang, Committee Member, Dr Xumu Zhang, Special Member.
Subjects/Keywords: synthesis; chiral ligand; asymmetric catalysis; transition metal
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Li, W. (2012). Design and Synthesis of Chiral Ligands and Their Applications in Transition Metal-catalyzed Asymmetric Reactions. (Thesis). Penn State University. Retrieved from https://submit-etda.libraries.psu.edu/catalog/12770
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Li, Wei. “Design and Synthesis of Chiral Ligands and Their Applications in Transition Metal-catalyzed Asymmetric Reactions.” 2012. Thesis, Penn State University. Accessed March 04, 2021.
https://submit-etda.libraries.psu.edu/catalog/12770.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Li, Wei. “Design and Synthesis of Chiral Ligands and Their Applications in Transition Metal-catalyzed Asymmetric Reactions.” 2012. Web. 04 Mar 2021.
Vancouver:
Li W. Design and Synthesis of Chiral Ligands and Their Applications in Transition Metal-catalyzed Asymmetric Reactions. [Internet] [Thesis]. Penn State University; 2012. [cited 2021 Mar 04].
Available from: https://submit-etda.libraries.psu.edu/catalog/12770.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Li W. Design and Synthesis of Chiral Ligands and Their Applications in Transition Metal-catalyzed Asymmetric Reactions. [Thesis]. Penn State University; 2012. Available from: https://submit-etda.libraries.psu.edu/catalog/12770
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Wayne State University
19.
Averill, Derek James.
Lanthanide-Based Precatalysts For Carbon-Carbon Bond-Forming Reactions In Aqueous Media.
Degree: PhD, Chemistry, 2014, Wayne State University
URL: https://digitalcommons.wayne.edu/oa_dissertations/1084
► The formation of carbon-carbon bonds is of great interest to synthetic chemists because these bonds make up the majority of biologically active compounds. The…
(more)
▼ The formation of carbon-carbon bonds is of great interest to synthetic chemists because these bonds make up the majority of biologically active compounds. The Mukaiyama aldol reaction is a Lewis-acid-catalyzed carbon-carbon bond-forming reaction that has the ability to produce optically active β-hydroxy carbonyls which can be found in many pharmaceuticals and natural products. Because of precatalyst instability towards hydrolysis, anhydrous solvents are commonly used. Recent efforts have focused on water-tolerant versions of enantioselective Mukaiyama aldol reactions because of the financial and environmental benefits of using aqueous media. Consequently, the Lewis-acidic and water-tolerant features of Ln
3+ ions have aroused great interest in lanthanide-catalyzed bond-forming reactions in aqueous media.
Several Ln
3+-based Lewis acid precatalysts that were designed for Mukaiyama aldol reactions have been shown to be enantioselective, water-tolerant, and recoverable. Limiting the usefulness of these precatalysts are high ligand loadings and long reaction times that are necessary for high enantiomeric ratios. An understanding of water-coordination number, counter anion identitiy, solvent system, and ligand type effect(s) are necessary to improve upon existing Ln
3+-based precatalysts.
I used luminescence-decay measurements and high performance liquid chromatography analyses to study the effects of water-coordination number, counter anion identitiy, and solvent system on reaction rates of Mukaiyama aldol reactions. I found that higher water-coordination numbers and higher water compositions gave rise to more reactive precatalysts for Mukaiyama aldol reactions that were catalyzed by Eu
3+. I synthesized and characterized four new hexadentate ligands to study the effects of ligand type on reactivity and selectivity of Eu
3+-based precatalysts for Mukaiyama aldol reactions. I used Eu
3+ emission spectra and
1H-NMR experiments to study changes in Eu
3+ coordination while titrating hexadentate ligands into solutions of Eu
3+ and I found that Eu
3+ is able to be coordinatively saturated in the presence of excess hexadentate ligands.
By studying Eu
3+ in the presence of different anions and several chiral hexadentate ligands that contain ester, carboxylic acid, alcohol and amide donating groups I was able to find trends in reactivity and selectivity. In this thesis I describe the results that are likely to contribute to the development of highly reactive and selective Ln
3+-based precatalysts.
Advisors/Committee Members: Matthew J. Allen.
Subjects/Keywords: Aqueous; Asymmetric; Catalysis; Europium; Lanthanide; Mukaiyama; Chemistry
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Averill, D. J. (2014). Lanthanide-Based Precatalysts For Carbon-Carbon Bond-Forming Reactions In Aqueous Media. (Doctoral Dissertation). Wayne State University. Retrieved from https://digitalcommons.wayne.edu/oa_dissertations/1084
Chicago Manual of Style (16th Edition):
Averill, Derek James. “Lanthanide-Based Precatalysts For Carbon-Carbon Bond-Forming Reactions In Aqueous Media.” 2014. Doctoral Dissertation, Wayne State University. Accessed March 04, 2021.
https://digitalcommons.wayne.edu/oa_dissertations/1084.
MLA Handbook (7th Edition):
Averill, Derek James. “Lanthanide-Based Precatalysts For Carbon-Carbon Bond-Forming Reactions In Aqueous Media.” 2014. Web. 04 Mar 2021.
Vancouver:
Averill DJ. Lanthanide-Based Precatalysts For Carbon-Carbon Bond-Forming Reactions In Aqueous Media. [Internet] [Doctoral dissertation]. Wayne State University; 2014. [cited 2021 Mar 04].
Available from: https://digitalcommons.wayne.edu/oa_dissertations/1084.
Council of Science Editors:
Averill DJ. Lanthanide-Based Precatalysts For Carbon-Carbon Bond-Forming Reactions In Aqueous Media. [Doctoral Dissertation]. Wayne State University; 2014. Available from: https://digitalcommons.wayne.edu/oa_dissertations/1084

Universidade Nova
20.
Zalewska, Karolina Anna Maria.
Development of novel ionic liquids based on biological molecules.
Degree: 2015, Universidade Nova
URL: http://www.rcaap.pt/detail.jsp?id=oai:run.unl.pt:10362/14075
► Ionic Liquids (ILs) belong to a class of compounds with unusual properties: very low vapour pressure; high chemical and thermal stability and the ability to…
(more)
▼ Ionic Liquids (ILs) belong to a class of compounds with unusual properties: very low vapour pressure; high chemical and thermal stability and the ability to dissolve a wide range of substances. A new field in research is evaluating the possibility to use natural chiral biomolecules for the preparation of chiral ionic liquids (CILs). This important challenge in synthetic chemistry can open new avenues of research in order to avoid some problems related with the intrinsic biodegradability and toxicity associated to conventional ILs.
The research work developed aimed for the synthesis of CILs, their characterization and possible applications, based on biological moieties used either as chiral cations or anions, depending on the synthetic manipulation of the derivatives. Overall, a total of 28 organic salts, including CILs were synthesized: 9 based on L-cysteine derivatives, 12 based on L-proline, 3 based on nucleosides and 4 based on nucleotides. All these new CILs were completely characterized and their chemical and physical properties were evaluated. Some CILs based on L-cysteine have been applied for discrimination processes, including resolution of racemates and as a chiral catalyst for
asymmetric Aldol condensation. L-proline derived CILs were also studied as chiral catalysts for Michael reaction.
In parallel, the interactions of macrocyclic oligosugars called cyclodextrins (CDs) with several ILs were studied. It was possible to improve the solubility of CDs in water and serum. Additionally, fatty acids and steroids showed an increase in water solubility when ILs-CDs systems were used. The development of efficient and selective ILs-CDs systems is indispensable to expand the range of their applications in host-guest interactions, drug delivery systems or catalytic reactions.
Novel salts derived from nucleobases were used in order to enhance the fluorescence in aqueous solution.
Additionally, preliminary studies regarding ethyl lactate as an alternative solvent for
asymmetric organocatalysis were performed.
Advisors/Committee Members: Branco, Luís.
Subjects/Keywords: Ionic liquids; Biological molecules; Chirality; Asymmetric catalysis
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
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APA (6th Edition):
Zalewska, K. A. M. (2015). Development of novel ionic liquids based on biological molecules. (Thesis). Universidade Nova. Retrieved from http://www.rcaap.pt/detail.jsp?id=oai:run.unl.pt:10362/14075
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Zalewska, Karolina Anna Maria. “Development of novel ionic liquids based on biological molecules.” 2015. Thesis, Universidade Nova. Accessed March 04, 2021.
http://www.rcaap.pt/detail.jsp?id=oai:run.unl.pt:10362/14075.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Zalewska, Karolina Anna Maria. “Development of novel ionic liquids based on biological molecules.” 2015. Web. 04 Mar 2021.
Vancouver:
Zalewska KAM. Development of novel ionic liquids based on biological molecules. [Internet] [Thesis]. Universidade Nova; 2015. [cited 2021 Mar 04].
Available from: http://www.rcaap.pt/detail.jsp?id=oai:run.unl.pt:10362/14075.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Zalewska KAM. Development of novel ionic liquids based on biological molecules. [Thesis]. Universidade Nova; 2015. Available from: http://www.rcaap.pt/detail.jsp?id=oai:run.unl.pt:10362/14075
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Colorado State University
21.
Glover, Garrett S.
Development of an asymmetric intermolecular stetter reaction and organocatalyst design.
Degree: MS(M.S.), Chemistry, 2012, Colorado State University
URL: http://hdl.handle.net/10217/88358
► The intermolecular Stetter represents a powerful carbon-carbon bond forming reaction that involves addition of an acyl anion equivalent to an untethered Michael acceptor. Despite the…
(more)
▼ The intermolecular Stetter represents a powerful carbon-carbon bond forming reaction that involves addition of an acyl anion equivalent to an untethered Michael acceptor. Despite the appeal of rendering the intermolecular reaction
asymmetric, this area remains particularly underdeveloped. We describe a catalytic
asymmetric intermolecular Stetter reaction for the coupling of 2-pyridinecarboxaldehydes and β-substituted vinyl triflones. In pursuit of increasing the efficiency of this reaction, we developed a series of base-activated NHC pre-catalysts that are capable of catalyzing the intramolecular Stetter reaction without an external base. As an indirect result of our attempts to form activated pre-catalysts, we discovered a catalyst hydration product, that itself generates free-carbene in solution. Additionally, we gathered conclusive evidence for a previously unknown SNAR type decomposition pathway of an electron deficient triazolinylidene catalyst.
Advisors/Committee Members: Rovis, Tomislav (advisor), Wood, John L. (committee member), Kanatous, Shane (committee member).
Subjects/Keywords: asymmetric catalysis; Stetter reaction; organocatalysis; NHC; intermolecular
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Glover, G. S. (2012). Development of an asymmetric intermolecular stetter reaction and organocatalyst design. (Masters Thesis). Colorado State University. Retrieved from http://hdl.handle.net/10217/88358
Chicago Manual of Style (16th Edition):
Glover, Garrett S. “Development of an asymmetric intermolecular stetter reaction and organocatalyst design.” 2012. Masters Thesis, Colorado State University. Accessed March 04, 2021.
http://hdl.handle.net/10217/88358.
MLA Handbook (7th Edition):
Glover, Garrett S. “Development of an asymmetric intermolecular stetter reaction and organocatalyst design.” 2012. Web. 04 Mar 2021.
Vancouver:
Glover GS. Development of an asymmetric intermolecular stetter reaction and organocatalyst design. [Internet] [Masters thesis]. Colorado State University; 2012. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10217/88358.
Council of Science Editors:
Glover GS. Development of an asymmetric intermolecular stetter reaction and organocatalyst design. [Masters Thesis]. Colorado State University; 2012. Available from: http://hdl.handle.net/10217/88358

Colorado State University
22.
Filloux, Claire M.
Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity.
Degree: PhD, Chemistry, 2015, Colorado State University
URL: http://hdl.handle.net/10217/166906
► The chapters that follow describe two independent investigations. Both relay the development of experimental methods for the catalytic, asymmetric addition of carbon-hydrogen bonds to alkenes.…
(more)
▼ The chapters that follow describe two independent investigations. Both relay the development of experimental methods for the catalytic,
asymmetric addition of carbon-hydrogen bonds to alkenes. In the first chapter, nucleophilic amine and N-heterocyclic carbene cocatalysts cooperate in the organocatalytic, cascade synthesis of benzofuranone products in good yields and high enantioselectivities. Importantly, the cascade protocol is found to outperform a two-pot procedure in which reaction intermediates are isolated and purified before the second step. Mechanistic studies reveal that additives and geometry of an olefin intermediate crucially influence reaction enantioselectivity. In the second method, a bulky Rh(I)-bisphosphine complex catalyzes the
asymmetric, intermolecular addition of benzoxazoles to methacrylate derivatives in fair to excellent yields and good to excellent enantioselectivities. Detailed deuterium labeling and epimerization studies provide considerable insight into the reaction mechanism: C-H activation is reversible; migratory insertion is likely enantiodetermining; and the bulky- bisphosphine ligand likely boosts reactivity and selectivity by discouraging deleterious ligation of benzoxazole starting materials to on- or off-cycle rhodium complexes and by impeding coordination-induced product epimerization.
Advisors/Committee Members: Rovis, Tomislav (advisor), McNaughton, Brian R. (committee member), Prieto, Amy L. (committee member), Crans, Debbie C. (committee member), Hentges, Shane T. (committee member).
Subjects/Keywords: catalysis; organic; asymmetric; rhodium; N-heterocyclic carbene
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Filloux, C. M. (2015). Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/166906
Chicago Manual of Style (16th Edition):
Filloux, Claire M. “Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity.” 2015. Doctoral Dissertation, Colorado State University. Accessed March 04, 2021.
http://hdl.handle.net/10217/166906.
MLA Handbook (7th Edition):
Filloux, Claire M. “Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity.” 2015. Web. 04 Mar 2021.
Vancouver:
Filloux CM. Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity. [Internet] [Doctoral dissertation]. Colorado State University; 2015. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10217/166906.
Council of Science Editors:
Filloux CM. Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity. [Doctoral Dissertation]. Colorado State University; 2015. Available from: http://hdl.handle.net/10217/166906

Boston College
23.
Coombs, John Ryan.
Platinum-Catalyzed Enantioselective Diboration of Terminal
Alkenes and Vinyl Boronates: Construction of Multiborylated
Compounds for Asymmetric Synthesis.
Degree: PhD, Chemistry, 2015, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:104624
► This dissertation will discuss in depth four main projects pertaining to the synthesis and utility of organoboronates for the construction of enantioenriched small molecules. First,…
(more)
▼ This dissertation will discuss in depth four main
projects pertaining to the synthesis and utility of organoboronates
for the construction of enantioenriched small molecules. First,
reaction optimization and substrate scope expansion of the
platinum-catalyzed enantioselective diboration of alkenes are
reported. Based on extensive experimental and computational
mechanistic analysis, a preliminary stereochemical model is also
proposed. A practical boron-Wittig reaction is presented in which
synthetically challenging di- and trisubstituted vinyl boronates
can be accessed in a highly stereoselective fashion from readily
available starting materials. The enantioselective diboration of
cis- and trans-vinyl boronates furnished novel 1,1,2-tris(boronate)
esters in up to 95:5 er. The intermediate tris(boronate) esters
were employed successfully in deborylative alkylations to furnish
enantioenriched internal vicinal bis(boronates) in excellent
diasteoselectivity. In the final chapter, an enantioselective
palladium-catalyzed intramolecular Suzuki-Miyaura coupling between
allyl boronates and aryl electrophiles is disclosed. The newly
developed transformation provides enantioenriched 5, 6, and
7-membered carbocycles in up to 93:7 er.
Advisors/Committee Members: James P. Morken (Thesis advisor).
Subjects/Keywords: Asymmetric Catalysis; Boron-Wittig Reaction; Diboration
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Coombs, J. R. (2015). Platinum-Catalyzed Enantioselective Diboration of Terminal
Alkenes and Vinyl Boronates: Construction of Multiborylated
Compounds for Asymmetric Synthesis. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:104624
Chicago Manual of Style (16th Edition):
Coombs, John Ryan. “Platinum-Catalyzed Enantioselective Diboration of Terminal
Alkenes and Vinyl Boronates: Construction of Multiborylated
Compounds for Asymmetric Synthesis.” 2015. Doctoral Dissertation, Boston College. Accessed March 04, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:104624.
MLA Handbook (7th Edition):
Coombs, John Ryan. “Platinum-Catalyzed Enantioselective Diboration of Terminal
Alkenes and Vinyl Boronates: Construction of Multiborylated
Compounds for Asymmetric Synthesis.” 2015. Web. 04 Mar 2021.
Vancouver:
Coombs JR. Platinum-Catalyzed Enantioselective Diboration of Terminal
Alkenes and Vinyl Boronates: Construction of Multiborylated
Compounds for Asymmetric Synthesis. [Internet] [Doctoral dissertation]. Boston College; 2015. [cited 2021 Mar 04].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:104624.
Council of Science Editors:
Coombs JR. Platinum-Catalyzed Enantioselective Diboration of Terminal
Alkenes and Vinyl Boronates: Construction of Multiborylated
Compounds for Asymmetric Synthesis. [Doctoral Dissertation]. Boston College; 2015. Available from: http://dlib.bc.edu/islandora/object/bc-ir:104624

Universitat Rovira i Virgili
24.
Alza Barrios, Esther.
Approaches to asymmetric catalysis with polymer-supported pyrrolidines.
Degree: Departament de Química Analítica i Química Orgànica, 2011, Universitat Rovira i Virgili
URL: http://hdl.handle.net/10803/37362
► The present research project developed is focused in the immobilization of catalytic systems allowing the formation of carbon-carbon and carbonheteroatom bonds through enantioselective procedures with…
(more)
▼ The present research project developed is focused in the immobilization of
catalytic systems allowing the formation of carbon-carbon and carbonheteroatom
bonds through enantioselective procedures with improved
sustainability characteristics (suppression of catalyst separation steps,
preferential use of water as a solvent under aerobic conditions, avoidance of
protecting groups and, hence, of protection and deprotection steps). In
particular, the study is directed towards the organocatalysis field, although
also
asymmetric catalytic processes mediated by metal complexes have been
developed. The approach introduced by our group combines the
optimization of the catalytic properties of the ligands, which is greatly
facilitated by their modular nature, with a design principle consisting in
performing the anchoring to the polymer through auxiliary functional
groups, positioned on the ligand molecule for minimal perturbation of the
catalytic site. In this manner, we have been able to develop polymersupported
ligands that do not show any decrease in catalytic activity or in
enantioselectivity with respect to their homogeneous counterparts. The
usual anchoring strategy used is the Cu-catalyzed azide/alkyne 1,3 dipolar
cycloaddition. In this manner, in this work proline and pyrrolidine
derivatives have been synthesized to catalyze organic transformations via
enamine and iminium ion mechanisms as Mannich or Michael reactions.
Organocatalytic cascade process has also been reported as useful method
for the preparation of highly functionalized cyclohexane derivatives in a
straightforward and efficient manner and the use of supported
organocatalysts has allowed us to implement this reactions not only in batch
processes but also in continuous flow conditions obtaining large amount of
desired product with high enantiopurity.
As have been mentioned,
asymmetric catalysis mediated by metal complexes
has been investigated. One project collect the study of the
asymmetric
reduction of ketones with borane and oxazaborolidine type catalysts as
aminoalcohols in homogeneous phase and the application of
diphenylprolinol derivatives supported on polymers by click-chemistry or by
direct nucleophilic substitution to the Merrifield resin. It is verified
experimentally that the triazole ring formed by anchoring the monomer to
the polymer matrix by click reaction has an important role in the selectivity
of the catalyst because leads to a not enantioselective path due to the boron
coordination to the triazole. When triazole ring is not present, aromatic
ketones are reduced with high enantioselectivities (90-99%) and complete
conversion after 30 minutes of reaction with qualitative yield because the
easy removing of the catalyst from the product by filtration.
Also a series of new modular Ru/aminoalcohol systems has been developed
and used as enantioselective catalysts in the
asymmetric transfer
hydrogenation reaction of ketones in both water and 2-propanol. The
catalytic behaviour exhibited in these two media…
Advisors/Committee Members: [email protected] (authoremail), false (authoremailshow), Pericàs i Brondo, Miquel A. (Miquel Àngel) (director), Sayalero, Sonia (codirector), true (authorsendemail).
Subjects/Keywords: Asymmetric catalysis; Organocatalysis; Supported catalysts; 54; 547
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Alza Barrios, E. (2011). Approaches to asymmetric catalysis with polymer-supported pyrrolidines. (Thesis). Universitat Rovira i Virgili. Retrieved from http://hdl.handle.net/10803/37362
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Alza Barrios, Esther. “Approaches to asymmetric catalysis with polymer-supported pyrrolidines.” 2011. Thesis, Universitat Rovira i Virgili. Accessed March 04, 2021.
http://hdl.handle.net/10803/37362.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Alza Barrios, Esther. “Approaches to asymmetric catalysis with polymer-supported pyrrolidines.” 2011. Web. 04 Mar 2021.
Vancouver:
Alza Barrios E. Approaches to asymmetric catalysis with polymer-supported pyrrolidines. [Internet] [Thesis]. Universitat Rovira i Virgili; 2011. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10803/37362.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Alza Barrios E. Approaches to asymmetric catalysis with polymer-supported pyrrolidines. [Thesis]. Universitat Rovira i Virgili; 2011. Available from: http://hdl.handle.net/10803/37362
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

National University of Ireland – Galway
25.
Mc Cleary, Nadine.
Design, synthesis and catalytic activity of novel oxazoline based ligands
.
Degree: 2015, National University of Ireland – Galway
URL: http://hdl.handle.net/10379/5210
► This thesis can be viewed as two separate studies. Firstly, the design, synthesis and catalytic activity of novel 2-pyridyl mono(oxazoline). A family of mono(oxazoline) ligands…
(more)
▼ This thesis can be viewed as two separate studies. Firstly, the design, synthesis and catalytic activity of novel 2-pyridyl mono(oxazoline). A family of mono(oxazoline) ligands were developed in which the 5-poition is substituted with various substituted esters. These ligands were then applied as organocatalysts in an
asymmetric hydrosilylation reaction and an
asymmetric allylation reaction.
Mono(oxazoline) ligands catalysed a benchmark hydrosilylation reaction and ee's of up to 46 to 48% were obtained. The ligands in which either the adamantyl ester, p nitro phenyl ester, p-chloro phenyl ester or the p-methyl phenyl ester were present afforded these results. Use of the ligands in a benchmark allylation reaction showed low conversions.
Preliminary modifications to the backbone structure were also undertaken in order to ascertain the dendicity of the ligands. It was found the ligands coordinate in a bidentate fashion.
The second part of the this study involved the design and attempted synthesis of 2nd generation 4,4'-bis(oxazoline) ligands. Structural modifications were proposed in order to increase selectivity from that of the first generation of ligands within this class. Our first proposed modification was the addition of secondary binding sites on the pendant groups on the ligand. Attempted ligand formation a novel one-pot deprotection-activation-ring-closure (DARC) reaction, was not successful.
The second proposed modification was the installation of a functionalised bridgehead. Racemisation issues lead to the formation of diastereomeric pairs in which separate was not possible, and the synthesis of the desired ligand proved unsuccessful. This and other synthetic results are discussed herein.
Advisors/Committee Members: O'Leary, Patrick (advisor).
Subjects/Keywords: Asymmetric catalysis;
Organic synthesis;
School of Chemistry
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Mc Cleary, N. (2015). Design, synthesis and catalytic activity of novel oxazoline based ligands
. (Thesis). National University of Ireland – Galway. Retrieved from http://hdl.handle.net/10379/5210
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Mc Cleary, Nadine. “Design, synthesis and catalytic activity of novel oxazoline based ligands
.” 2015. Thesis, National University of Ireland – Galway. Accessed March 04, 2021.
http://hdl.handle.net/10379/5210.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Mc Cleary, Nadine. “Design, synthesis and catalytic activity of novel oxazoline based ligands
.” 2015. Web. 04 Mar 2021.
Vancouver:
Mc Cleary N. Design, synthesis and catalytic activity of novel oxazoline based ligands
. [Internet] [Thesis]. National University of Ireland – Galway; 2015. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10379/5210.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Mc Cleary N. Design, synthesis and catalytic activity of novel oxazoline based ligands
. [Thesis]. National University of Ireland – Galway; 2015. Available from: http://hdl.handle.net/10379/5210
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

National University of Ireland – Galway
26.
Kellehan, David.
Synthesis and Application of Chiral AraBOX ligands for Asymmetric Catalysis
.
Degree: 2012, National University of Ireland – Galway
URL: http://hdl.handle.net/10379/3405
► This thesis deals with the design, synthesis and reactivity of novel 4,4'-bisoxazoline ligands and their metal complexes; (S,S)-MePrAraBOX, (S,S)-PhPrAraBOX, (S,R)-MePrAraBOX, (S,R)-PhPrAraBOX, (S,R)-BnOAcAraBOX and (S,R)-BnOHAraBOX. Metal…
(more)
▼ This thesis deals with the design, synthesis and reactivity of novel 4,4'-bisoxazoline ligands and their metal complexes; (S,S)-MePrAraBOX, (S,S)-PhPrAraBOX, (S,R)-MePrAraBOX, (S,R)-PhPrAraBOX, (S,R)-BnOAcAraBOX and (S,R)-BnOHAraBOX. Metal complexes of these ligands have been applied to transition metal catalysed
asymmetric reactions, in particular
asymmetric Diels Alder, cyclopropanation and allylic alkylation reactions.
A copper(II) complex of (S,R)-PhPrAraBOX catalysed a benchmark Diels Alder reaction in up to 57% ee, the highest enantioselectivity yet achieved for a 4,4'-BOX ligand in a Diels Alder reaction. An ee of 70% was achieved with a copper(I) complex of (S,S)-MePrAraBOX in a benchmark
asymmetric cyclopropanation reaction, which is also the highest enantioselectivity yet achieved for a 4,4'-BOX ligand in these reactions. The ligands were also applied to the
asymmetric allylic alkylation reaction. They were the first 4,4'-BOX ligands to generate enantiocontrol in the reaction, with a palladium complex of (S,S)-MePrAraBOX producing an ee of 72%. The rationalisation of these results, in particular the results relating to the cyclopropanation reaction, are supported by computational studies carried out by colleagues in Zaragoza.
The 4,4'-bisoxazoline ligands (S,R)-BnOAcAraBOX and (S,R)-BnOHAraBOX, which contain secondary binding sites, were applied to the Diels Alder and
asymmetric allylic alkylation reactions with low activity and selectivity. Ligand (S,R)-BnOHAraBOX was also applied to an
asymmetric alkylation of benzaldehyde, showing low conversion and no selectivity.
Chapter One deals with the introduction of the general concepts of
asymmetric synthesis and
asymmetric catalysis. Chapter Two discusses the synthesis of the 4,4'-bisoxazoline ligands and the application of the metal complexes of these ligands to the
asymmetric reactions. Chapter Three contains the full experimental details for the project, including spectral and analytical data.
Advisors/Committee Members: O'Leary, Patrick (advisor).
Subjects/Keywords: Bisoxazoline ligands;
Asymmetric catalysis;
Department of Chemistry
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Kellehan, D. (2012). Synthesis and Application of Chiral AraBOX ligands for Asymmetric Catalysis
. (Thesis). National University of Ireland – Galway. Retrieved from http://hdl.handle.net/10379/3405
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Kellehan, David. “Synthesis and Application of Chiral AraBOX ligands for Asymmetric Catalysis
.” 2012. Thesis, National University of Ireland – Galway. Accessed March 04, 2021.
http://hdl.handle.net/10379/3405.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Kellehan, David. “Synthesis and Application of Chiral AraBOX ligands for Asymmetric Catalysis
.” 2012. Web. 04 Mar 2021.
Vancouver:
Kellehan D. Synthesis and Application of Chiral AraBOX ligands for Asymmetric Catalysis
. [Internet] [Thesis]. National University of Ireland – Galway; 2012. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/10379/3405.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Kellehan D. Synthesis and Application of Chiral AraBOX ligands for Asymmetric Catalysis
. [Thesis]. National University of Ireland – Galway; 2012. Available from: http://hdl.handle.net/10379/3405
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Toronto
27.
Smith, Samantha Alizabeth Michelle.
Asymmetric Hydrogenation Using Catalysts Based on Abundant Metals.
Degree: PhD, 2018, University of Toronto
URL: http://hdl.handle.net/1807/89841
► The design of chiral catalysts for hydrogenation chemistry is a field forever continuing as there are always improvements to be made, either in activity, selectivity,…
(more)
▼ The design of chiral catalysts for hydrogenation chemistry is a field forever continuing as there are always improvements to be made, either in activity, selectivity, or cost and toxicity of catalysts. This dissertation focuses on the design and synthesis of new base-metal catalysts with the intention to improve the activity and selectivity of
asymmetric hydrogenation reactions. This was approached with the following goals in mind: the improvement of syntheses of current catalysts to reduce the cost or to decrease the harshness of catalytic conditions required, the variation of phosphine donors for insight into the mechanism and to use such data to assist in the future rational design of new catalysts, and the use of other less-used abundant first row transition metals to explore the limits of such metals in hydrogenation chemistry. Each of the chapters discussed, with the exception of Chapter 1, describes the findings of new catalysts which were synthesized following one or more of the goals outlined and how they differ from previously reported related complexes, both fundamentally in their molecular structures as well as their activity and selectivity in the
asymmetric hydrogenation of ketones. New
asymmetric transfer hydrogenation catalysts were synthesized following our previous reports with a series of phosphorus donors. This resulted in an increase in enantioselectivity of the product alcohols at the cost of lower activity. An improvement of synthesis and variation of donors for pincer iron catalysts applied in the
asymmetric pressure hydrogenation of ketones resulted in an increase in enantioselectivity; however slightly higher pressures of H2 gas were required for complete conversion (10 vs 5 bar). Manganese analogues of the previously mentioned pincer complexes were discovered to be active in the
asymmetric pressure hydrogenation of ketones. These complexes required higher pressures and temperatures than their iron counterparts, but we did see an improvement of catalytic results when comparing to other manganese hydrogenation catalysts recently reported since our catalysts operate at lower temperatures, pressures, and shorter reaction times. An iron complex bearing a new chiral, bidentate, and protic NHC-PPh2 ligand was synthesized for the
asymmetric transfer hydrogenation of acetophenone. This complex requires UV-irradiation for
catalysis.
Advisors/Committee Members: Morris, Robert H, Chemistry.
Subjects/Keywords: abundant metals; asymmetric; catalysis; hydrogenation; 0488
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Smith, S. A. M. (2018). Asymmetric Hydrogenation Using Catalysts Based on Abundant Metals. (Doctoral Dissertation). University of Toronto. Retrieved from http://hdl.handle.net/1807/89841
Chicago Manual of Style (16th Edition):
Smith, Samantha Alizabeth Michelle. “Asymmetric Hydrogenation Using Catalysts Based on Abundant Metals.” 2018. Doctoral Dissertation, University of Toronto. Accessed March 04, 2021.
http://hdl.handle.net/1807/89841.
MLA Handbook (7th Edition):
Smith, Samantha Alizabeth Michelle. “Asymmetric Hydrogenation Using Catalysts Based on Abundant Metals.” 2018. Web. 04 Mar 2021.
Vancouver:
Smith SAM. Asymmetric Hydrogenation Using Catalysts Based on Abundant Metals. [Internet] [Doctoral dissertation]. University of Toronto; 2018. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/1807/89841.
Council of Science Editors:
Smith SAM. Asymmetric Hydrogenation Using Catalysts Based on Abundant Metals. [Doctoral Dissertation]. University of Toronto; 2018. Available from: http://hdl.handle.net/1807/89841

University of Toronto
28.
Kim, Byoungmoo.
Asymmetric Lactone Synthesis via Hydroacylation and Stereoselective Cyclic Peptide Synthesis via Hydrogenation.
Degree: PhD, 2014, University of Toronto
URL: http://hdl.handle.net/1807/71059
► Asymmetric transition metal catalysis has benefited human health by greatly facilitating access to natural products and therapeutic drugs. However, scientists continue to face challenges of…
(more)
▼ Asymmetric transition metal catalysis has benefited human health by greatly facilitating access to natural products and therapeutic drugs. However, scientists continue to face challenges of developing more direct processes while minimizing the generation of unwanted wastes. As there is a high demand in the development of sustainable and atom-economical processes, the focus of my doctoral studies was to apply asymmetric catalysis in the development of conceptually unique and sustainable strategies for the synthesis of biologically important organic molecules. This dissertation includes: 1) the development of Rh-catalyzed enantioselective ketone hydroacylation as an atom-economical and general method for the synthesis of phthalide, 2) nickel catalyzed olefin hydroesterification for the synthesis of all-carbon quaternary stereocenters, and 3) a new synthetic strategy for preparing cyclic peptides using asymmetric hydrogenation.
2015-12-18 00:00:00
Advisors/Committee Members: Dong, Vy M, Chemistry.
Subjects/Keywords: Asymmetric catalysis; Cyclic peptide; Lactone; Rhoidum; 0485
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Kim, B. (2014). Asymmetric Lactone Synthesis via Hydroacylation and Stereoselective Cyclic Peptide Synthesis via Hydrogenation. (Doctoral Dissertation). University of Toronto. Retrieved from http://hdl.handle.net/1807/71059
Chicago Manual of Style (16th Edition):
Kim, Byoungmoo. “Asymmetric Lactone Synthesis via Hydroacylation and Stereoselective Cyclic Peptide Synthesis via Hydrogenation.” 2014. Doctoral Dissertation, University of Toronto. Accessed March 04, 2021.
http://hdl.handle.net/1807/71059.
MLA Handbook (7th Edition):
Kim, Byoungmoo. “Asymmetric Lactone Synthesis via Hydroacylation and Stereoselective Cyclic Peptide Synthesis via Hydrogenation.” 2014. Web. 04 Mar 2021.
Vancouver:
Kim B. Asymmetric Lactone Synthesis via Hydroacylation and Stereoselective Cyclic Peptide Synthesis via Hydrogenation. [Internet] [Doctoral dissertation]. University of Toronto; 2014. [cited 2021 Mar 04].
Available from: http://hdl.handle.net/1807/71059.
Council of Science Editors:
Kim B. Asymmetric Lactone Synthesis via Hydroacylation and Stereoselective Cyclic Peptide Synthesis via Hydrogenation. [Doctoral Dissertation]. University of Toronto; 2014. Available from: http://hdl.handle.net/1807/71059

University of New Mexico
29.
Song, Xixi.
Development of novel organocatalytic cascade reactions and application in organic systheses.
Degree: Department of Chemistry and Chemical Biology, 2012, University of New Mexico
URL: https://digitalrepository.unm.edu/chem_etds/24
► The development of new catalytic reactions, particularly synthetically efficient cascade processes for the facile preparation of important molecular architectures, which otherwise are difficult to access…
(more)
▼ The development of new catalytic reactions, particularly synthetically efficient cascade processes for the facile preparation of important molecular architectures, which otherwise are difficult to access via traditional methods, is of considerable significance. Toward this end, my Ph.D. work focuses on developing new organocatalytic reactions and their applications in organic syntheses. A novel direct organocatalytic stereoselective α-arylation methodology has been discovered. The cross-coupling-like products are assembled using simple enals and various brominated aromatic systems, such as p-bromophenols, bromonaphthols and 3-bromoindoles. The products have been applied in the concise photo-syntheses of [α]-annulated carbazoles. Moreover, an unexpected reaction has been identified with aliphatic enals, and fully developed into a new [3+3] formal cycloaddition cascade reaction, and serves as a powerful approach to polysubstituted arenes from simple enals in a highly regio- and chemo-selective fashion. The Diels-Alder reaction of acetylenic aldehydes has been realized for 'one-pot' synthesis of polysubstituted salicylaldehyde frameworks that were constructed via an unprecedented aminocatalytic Diels-Alder-retro-Diels-Alder cascade from simple alkynals and 2-pyrones. Furthermore, the use of N-protected 3-hydroxy-2-pyridines as dienes leads to catalytic enantioselective Diels-Alder process without subsequent retro-Diels-Alder reaction. A chiral C2 symmetric organocatalyst is found as an effective promoter for the activation and stereo-control of various substituted alkynals.
Advisors/Committee Members: Wang, Wei, Wang, Wei, Mariano, Patrick, Guo, Hua, Feng, Changjian.
Subjects/Keywords: organocatalysis; cascade reaction; asymmetric catalysis; aminocatalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Song, X. (2012). Development of novel organocatalytic cascade reactions and application in organic systheses. (Doctoral Dissertation). University of New Mexico. Retrieved from https://digitalrepository.unm.edu/chem_etds/24
Chicago Manual of Style (16th Edition):
Song, Xixi. “Development of novel organocatalytic cascade reactions and application in organic systheses.” 2012. Doctoral Dissertation, University of New Mexico. Accessed March 04, 2021.
https://digitalrepository.unm.edu/chem_etds/24.
MLA Handbook (7th Edition):
Song, Xixi. “Development of novel organocatalytic cascade reactions and application in organic systheses.” 2012. Web. 04 Mar 2021.
Vancouver:
Song X. Development of novel organocatalytic cascade reactions and application in organic systheses. [Internet] [Doctoral dissertation]. University of New Mexico; 2012. [cited 2021 Mar 04].
Available from: https://digitalrepository.unm.edu/chem_etds/24.
Council of Science Editors:
Song X. Development of novel organocatalytic cascade reactions and application in organic systheses. [Doctoral Dissertation]. University of New Mexico; 2012. Available from: https://digitalrepository.unm.edu/chem_etds/24

University of South Florida
30.
Tao, Jingran.
Asymmetric Nitrene Transfer Reactions with Azides via Co(II)-Based Metalloradical Catalysis (MRC).
Degree: 2013, University of South Florida
URL: https://scholarcommons.usf.edu/etd/4590
► Asymmetric nitrene transfer reactions via metalloradical catalysis (MRC) with azides has attracted research interest because of its fundamental and practical importance. The resulting nitrogen-containing units…
(more)
▼ Asymmetric nitrene transfer reactions via metalloradical catalysis (MRC) with
azides has attracted research interest because of its fundamental and practical importance.
The resulting nitrogen-containing units are recurrent motifs in biologically important
molecules and can serve as versatile precursors in organic synthesis.
The [Co(D2-Por*)] have emerged as a new class of catalysts for asymmetric
aziridination and C-H amination. These metalloradical catalysts have been shown to be
highly effective for the asymmetric intermolecular aziridination of a broad scope of
substrates with different classes of azides with excellent to good enantioselectivity. The
intramolecular C-H amination utilizing various azides can allow for the construction of
diverse nitrogen containing heterocyclic compounds.
Subjects/Keywords: asymmetric; azide; aziridination; catalysis; cobalt; porphyrin; Chemistry
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Tao, J. (2013). Asymmetric Nitrene Transfer Reactions with Azides via Co(II)-Based Metalloradical Catalysis (MRC). (Thesis). University of South Florida. Retrieved from https://scholarcommons.usf.edu/etd/4590
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Tao, Jingran. “Asymmetric Nitrene Transfer Reactions with Azides via Co(II)-Based Metalloradical Catalysis (MRC).” 2013. Thesis, University of South Florida. Accessed March 04, 2021.
https://scholarcommons.usf.edu/etd/4590.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Tao, Jingran. “Asymmetric Nitrene Transfer Reactions with Azides via Co(II)-Based Metalloradical Catalysis (MRC).” 2013. Web. 04 Mar 2021.
Vancouver:
Tao J. Asymmetric Nitrene Transfer Reactions with Azides via Co(II)-Based Metalloradical Catalysis (MRC). [Internet] [Thesis]. University of South Florida; 2013. [cited 2021 Mar 04].
Available from: https://scholarcommons.usf.edu/etd/4590.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Tao J. Asymmetric Nitrene Transfer Reactions with Azides via Co(II)-Based Metalloradical Catalysis (MRC). [Thesis]. University of South Florida; 2013. Available from: https://scholarcommons.usf.edu/etd/4590
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
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