You searched for subject:(Enantioselective)
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1.
Wang, Sa.
Synthesis, Application, and Mechanistic Studies of the
Asymmetric Addition of Organozinc Reagents to
3,4-Dihydroisoquinoline N-Oxide.
Degree: PhD, Chemistry, 2009, Brown University
URL: https://repository.library.brown.edu/studio/item/bdr:234/
► Tetrahydroisoquinolines (THIQ) are an important structural motif in many alkaloids, and they display significant biological and pharmacological properties. A majority of these compounds possess a…
(more)
▼ Tetrahydroisoquinolines (THIQ) are an important
structural motif in many alkaloids, and they display significant
biological and pharmacological properties. A majority of these
compounds possess a chiral center at the C-1 position, while
stereoisomers at this position exhibit very different activities.
Thus, the
enantioselective synthesis of 1-substituted-THIQs is of
great interest to both organic and medicinal chemists. In this
thesis, we first report the
enantioselective addition of vinylzinc
reagents to 3,4-dihydroisoquinoline N-oxide. With an
N-acylethylenediamine ligand as the catalyst, we obtained a group
of chiral N-hydroxyl-1-vinyl-THIQs in 62-85% yield and 90-95% ee. A
variety of aliphatic, cyclic and aromatic vinylzinc reagents were
employed in the reaction. This method was used to synthesize a
single enantiomer of the unnatural amino acid
N-Cbz-D-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid. Next, we
describe a novel, expedient synthesis of chiral 1-aryl-THIQs, in
which the key step is the asymmetric addition of arylzinc reagents
to 3,4-dihydroisoquinoline N-oxide catalyzed by the diamine ligand.
With aryl pinacolyl boronic esters as arylzinc precursors, we
achieved good yields (35-99%) and excellent enantioselectivities
(97-99% ee) in the reaction. This methodology was demonstrated
through the
enantioselective synthesis of the GlaxoSmithKline drug
? Solifenacin. Finally, we investigated the mechanism of the
enantioselective addition of arylzinc reagents to
3,4-dihydroisoquinoline N-oxide. We adopted a systematic strategy
to study this complex system by using a wide range of NMR
techniques. This includes, 1D and 2D NMR, Diffusion-Order NMR
spectroscopy, Job plot, NMR titration, and in-situ NMR kinetic
measurement. Through these studies, we obtained information about
the structure and molecular interactions of reactive intermediates
along the reaction pathway. We also found that the reaction occurs
via a binuclear-zinc intermediate. Comparison of reaction rates
showed that the catalyzed arylation reaction proceeds faster than
the non-catalyzed process. Altogether, we propose a catalytic cycle
for the asymmetric arylation reaction. The preference for formation
of the (S)-product was rationalized by examining the conformations
of different transition states.
Advisors/Committee Members: Seto, Christopher (director), Williard, Paul (reader), Zimmt, Matthew (reader).
Subjects/Keywords: enantioselective synthesis
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APA (6th Edition):
Wang, S. (2009). Synthesis, Application, and Mechanistic Studies of the
Asymmetric Addition of Organozinc Reagents to
3,4-Dihydroisoquinoline N-Oxide. (Doctoral Dissertation). Brown University. Retrieved from https://repository.library.brown.edu/studio/item/bdr:234/
Chicago Manual of Style (16th Edition):
Wang, Sa. “Synthesis, Application, and Mechanistic Studies of the
Asymmetric Addition of Organozinc Reagents to
3,4-Dihydroisoquinoline N-Oxide.” 2009. Doctoral Dissertation, Brown University. Accessed April 13, 2021.
https://repository.library.brown.edu/studio/item/bdr:234/.
MLA Handbook (7th Edition):
Wang, Sa. “Synthesis, Application, and Mechanistic Studies of the
Asymmetric Addition of Organozinc Reagents to
3,4-Dihydroisoquinoline N-Oxide.” 2009. Web. 13 Apr 2021.
Vancouver:
Wang S. Synthesis, Application, and Mechanistic Studies of the
Asymmetric Addition of Organozinc Reagents to
3,4-Dihydroisoquinoline N-Oxide. [Internet] [Doctoral dissertation]. Brown University; 2009. [cited 2021 Apr 13].
Available from: https://repository.library.brown.edu/studio/item/bdr:234/.
Council of Science Editors:
Wang S. Synthesis, Application, and Mechanistic Studies of the
Asymmetric Addition of Organozinc Reagents to
3,4-Dihydroisoquinoline N-Oxide. [Doctoral Dissertation]. Brown University; 2009. Available from: https://repository.library.brown.edu/studio/item/bdr:234/

Boston College
2.
Zhang, Ping.
Enantioselective Catalysis Through 3,3'-reductive
Elimination of Unsaturated Allyl Metal Complexes.
Degree: PhD, Chemistry, 2012, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:101159
► This dissertation aims to design and develop novel and synthetically useful catalytic enantioselective C-C bond-forming reactions that employ a newly uncovered 3,3'-reductive elimination of bis(allyl)metal…
(more)
▼ This dissertation aims to design and develop novel and
synthetically useful catalytic
enantioselective C-C bond-forming
reactions that employ a newly uncovered 3,3'-reductive elimination
of bis(allyl)metal species. This elementary transformation allows
for new routes for the
enantioselective construction of a range of
important motifs found in natural products. Enantiomerically
enriched Z-allylic alcohols are readily accessed through the
Ni-catalyzed allylation of trans,trans-dienals. Importantly, the
first example of branch- and
enantioselective allyl-allyl
cross-coupling is presented as well, suitable for the construction
of compounds bearing tertiary and quaternary carbon centers. With
the aim to broaden the application of above described
transformations, this dissertation also presents the development of
highly efficient and convenient methods for the syntheses of
substituted and functionalized allylic boronates.
Advisors/Committee Members: James P. Morken (Thesis advisor).
Subjects/Keywords: Enantioselective catalysis
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APA ·
Chicago ·
MLA ·
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CSE |
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APA (6th Edition):
Zhang, P. (2012). Enantioselective Catalysis Through 3,3'-reductive
Elimination of Unsaturated Allyl Metal Complexes. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101159
Chicago Manual of Style (16th Edition):
Zhang, Ping. “Enantioselective Catalysis Through 3,3'-reductive
Elimination of Unsaturated Allyl Metal Complexes.” 2012. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:101159.
MLA Handbook (7th Edition):
Zhang, Ping. “Enantioselective Catalysis Through 3,3'-reductive
Elimination of Unsaturated Allyl Metal Complexes.” 2012. Web. 13 Apr 2021.
Vancouver:
Zhang P. Enantioselective Catalysis Through 3,3'-reductive
Elimination of Unsaturated Allyl Metal Complexes. [Internet] [Doctoral dissertation]. Boston College; 2012. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:101159.
Council of Science Editors:
Zhang P. Enantioselective Catalysis Through 3,3'-reductive
Elimination of Unsaturated Allyl Metal Complexes. [Doctoral Dissertation]. Boston College; 2012. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101159

Boston College
3.
Lee, Jaehee.
Expedient Synthesis of High-Value Organoboronates Through
Catalytic Enantioselective Alkene Functionalization.
Degree: PhD, Chemistry, 2017, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:107696
► Chapter 1 Mechanism-Based Enhancement of Scope and Enantioselectivity for Reactions Involving a Copper-Substituted Stereogenic Carbon Center: Organoborons are important building blocks of complex natural products,…
(more)
▼ Chapter 1 Mechanism-Based Enhancement of Scope and
Enantioselectivity for Reactions Involving a Copper-Substituted
Stereogenic Carbon Center: Organoborons are important building
blocks of complex natural products, functional materials, and
pharmaceutically relevant compounds due to their prevalent utility
in C–C and C–hetero atom bond transformations. Using a readily
accessible copper catalyst, we have developed highly site- and
enantioselective allylic substitution by way of a threecomponent,
single-vessel, and sustainable catalytic protocol. Detailed
mechanistic studies revealed valuable insights which led us to
develop copper–boron and copper–hydride additions to olefins with
broader substrate scope, higher efficiency, and higher
enantioselectivity. In addition, the method can be applied to the
synthesis of biologically active molecules such as preclamol and
heliespirone A and C. Chapter 2 Versatile Homoallylic Boronates by
Chemo-, SN2’-, Diastereo- and
Enantioselective Catalytic Sequence
of Cu–H Addition to Vinyl-B(pin)/Allylic Substitution: To achieve
an efficient multicomponent reaction, high chemoselectivity between
a starting material and a reagent must be accomplished during the
first catalytic transformation to generate an intermediate which
then selectively reacts with another substrate to furnish the
product in a site-, and/or stereoselective fashion. Development and
application of efficient multicomponent reactions involving allylic
substitution can provide alternative solutions for difficult
synthetic problems in organic chemistry. Our group has developed a
sulfonate-containing chiral NHC–Cu catalyzed chemo-, SN2’-,
diastereo-, and
enantioselective multicomponent reaction through
Cu–H addition to readily available vinyl–B(pin) followed by allylic
substitution to deliver homoallylic boronates. The derived
homoallylic alcohols can be used as building blocks of biologically
active molecules. Chapter 3 Enantioenriched Halogen-Substituted
Alkenes through NHC–Cu-Catalyzed Borylation/Dehalogenation and
Their Applications: Because of their unique properties, mono- and
difluoroalkenes have received attention as an important class of
compounds as building blocks for fluorine-containing monomers for
functional polymers and biologically active molecules in medicine
and agriculture. However, reported methods to prepare
enantioenriched difluoroalkenes are scarce and often require
undesirable amounts of precious transition metals and very high/low
temperatures. To solve these challenges, we have developed a highly
efficient, regio-, and
enantioselective boron allylic substitution
to CF3-alkenes and other halogen-substituted olefins by using an
abundant copper-based catalyst.
Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).
Subjects/Keywords: Enantioselective catalysis
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
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APA (6th Edition):
Lee, J. (2017). Expedient Synthesis of High-Value Organoboronates Through
Catalytic Enantioselective Alkene Functionalization. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:107696
Chicago Manual of Style (16th Edition):
Lee, Jaehee. “Expedient Synthesis of High-Value Organoboronates Through
Catalytic Enantioselective Alkene Functionalization.” 2017. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:107696.
MLA Handbook (7th Edition):
Lee, Jaehee. “Expedient Synthesis of High-Value Organoboronates Through
Catalytic Enantioselective Alkene Functionalization.” 2017. Web. 13 Apr 2021.
Vancouver:
Lee J. Expedient Synthesis of High-Value Organoboronates Through
Catalytic Enantioselective Alkene Functionalization. [Internet] [Doctoral dissertation]. Boston College; 2017. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:107696.
Council of Science Editors:
Lee J. Expedient Synthesis of High-Value Organoboronates Through
Catalytic Enantioselective Alkene Functionalization. [Doctoral Dissertation]. Boston College; 2017. Available from: http://dlib.bc.edu/islandora/object/bc-ir:107696

University of Manchester
4.
Page, Abigail.
Atropisomeric Diaryl Ethers and other Non-Biaryl
Atropisomers.
Degree: 2011, University of Manchester
URL: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:121988
► Atropisomerism is a property exhibited by molecules where rotation about one or more bonds is restricted. Along with biaryls, which are widely utilised in asymmetric…
(more)
▼ Atropisomerism is a property exhibited by molecules
where rotation about one or more bonds is restricted. Along with
biaryls, which are widely utilised in asymmetric catalysis, several
other classes of compounds display atropisomerism. These molecules
have applications in
enantioselective synthesis, asymmetric
catalysis and have been used to relay stereochemical information.
There are, however, a number of challenges associated with their
asymmetric synthesis (Chapter 1).This thesis describes research
carried out on the synthesis and asymmetric synthesis of
atropisomeric diaryl ethers. Chapter 2.1 explains how these ethers
are synthesised in multi-gram quantities and to allow the
incorporation of large ortho substituents.Having a number of diaryl
ethers with suitable substitution patterns to
achieveatropisomerism, Chapter 2.2 goes on to report two novel and
complimentarybiocatalytic approaches to the
enantioselective
synthesis of diaryl ethers bydesymmetrisation. This chapter also
describes a possible route towards the synthesis of a diaryl ether
based ligand.Chapter 2.3 reports the lateral lithiation of meso
diaryl ethers to yield diastereomeric atropisomers
stereoselectively. Our attempts to use (–)-sparteine in lateral
lithiations to desymmetrise a diaryl ether enantioselectively is
also described. We go on to determine the configurational integrity
of our organolithiums and the reaction pathway that exists in
lithium substitution.Finally, the diastereoselective synthesis of
both a diaryl ether (via a stereoselective reduction of a
pro-chiral ketone) and a diaryl sulfide (via an addition reaction)
is described in chapter 2.4. This chapter also reports the
conformational behaviour of a diaryl amide in
solution.
Advisors/Committee Members: Clayden, Jonathan.
Subjects/Keywords: Atropisomer; enantioselective synthesis
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
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Manager
APA (6th Edition):
Page, A. (2011). Atropisomeric Diaryl Ethers and other Non-Biaryl
Atropisomers. (Doctoral Dissertation). University of Manchester. Retrieved from http://www.manchester.ac.uk/escholar/uk-ac-man-scw:121988
Chicago Manual of Style (16th Edition):
Page, Abigail. “Atropisomeric Diaryl Ethers and other Non-Biaryl
Atropisomers.” 2011. Doctoral Dissertation, University of Manchester. Accessed April 13, 2021.
http://www.manchester.ac.uk/escholar/uk-ac-man-scw:121988.
MLA Handbook (7th Edition):
Page, Abigail. “Atropisomeric Diaryl Ethers and other Non-Biaryl
Atropisomers.” 2011. Web. 13 Apr 2021.
Vancouver:
Page A. Atropisomeric Diaryl Ethers and other Non-Biaryl
Atropisomers. [Internet] [Doctoral dissertation]. University of Manchester; 2011. [cited 2021 Apr 13].
Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:121988.
Council of Science Editors:
Page A. Atropisomeric Diaryl Ethers and other Non-Biaryl
Atropisomers. [Doctoral Dissertation]. University of Manchester; 2011. Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:121988

University of Utah
5.
Jensen, Katrina Helen.
Examination of catalyst and reactant electronic effects in enantioselective reactions.
Degree: PhD, Chemistry, 2010, University of Utah
URL: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2019/rec/949
► Given the potential for opposite enantiomers of a chiral molecule to have different biological effects, access to a single enantiomer of a compound is desirable.…
(more)
▼ Given the potential for opposite enantiomers of a chiral molecule to have different biological effects, access to a single enantiomer of a compound is desirable. Asymmetric catalysis is a powerful method for the synthesis of enantiomerically enriched chiral building blocks, and a mechanistic understanding of the relationship between catalyst structure and selectivity has the potential to advance the field. Additionally, mechanistic investigation provides insight about the nature of reactive intermediates, which allows one to imagine new ways to obtain or intercept such intermediates in the pursuit of new reaction development. Herein are described studies of two catalytic systems with a focus on mechanistic understanding. In the first system, a modular catalyst structure was used to systematically evaluate the effects of catalyst acidity in a hydrogen bond-catalyzed hetero Diels-Alder reaction. Linear free energy relationships between catalyst acidity and both rate and enantioselectivity were observed, where greater catalyst acidity leads to increased activity and selectivity. A relationship between reactant electronic nature and rate was also observed, although there is no such correlation to enantioselectivity, indicating the system is under catalyst control. In the second study, a unique approach to alkene difunctionalization was taken based on a mechanistic hypothesis of a quinone methide intermediate in a related reaction. Substrates containing an alkene adjacent to an ortho-phenol and a tethered nucleophile were prepared, allowing for the regioselective addition of two distinct nucleophiles. A key improvement to the catalytic system was achieved using a ligated copper cocatalyst, leading to improved reactivity without a detrimental effect on enantioselectivity. The reaction was applied to the dioxygenation and aminooxygenation of alkenes, resulting in the enantioselective formation of heterocyclic compounds bearing two adjacent chiral centers. The mechanism of the alkene difunctionalization reaction was studied using physical organic chemistry techniques. The proposed quinone methide intermediate was trapped in a Diels Alder reaction. Kinetic analysis provided evidence of rate limiting attack of this intermediate and for copper involvement in more than solely catalyst turnover. Through examination of substrate electronic effects a Jaffé relationship was observed correlating rate to electronic perturbation at two positions of the phenol. Ligand effects were evaluated to provide evidence of rapid ligand exchange and a direct correlation between ligand electronic nature and enantioselectivity.
Subjects/Keywords: Catalysis; Enantioselective; Organic chemistry
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Jensen, K. H. (2010). Examination of catalyst and reactant electronic effects in enantioselective reactions. (Doctoral Dissertation). University of Utah. Retrieved from http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2019/rec/949
Chicago Manual of Style (16th Edition):
Jensen, Katrina Helen. “Examination of catalyst and reactant electronic effects in enantioselective reactions.” 2010. Doctoral Dissertation, University of Utah. Accessed April 13, 2021.
http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2019/rec/949.
MLA Handbook (7th Edition):
Jensen, Katrina Helen. “Examination of catalyst and reactant electronic effects in enantioselective reactions.” 2010. Web. 13 Apr 2021.
Vancouver:
Jensen KH. Examination of catalyst and reactant electronic effects in enantioselective reactions. [Internet] [Doctoral dissertation]. University of Utah; 2010. [cited 2021 Apr 13].
Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2019/rec/949.
Council of Science Editors:
Jensen KH. Examination of catalyst and reactant electronic effects in enantioselective reactions. [Doctoral Dissertation]. University of Utah; 2010. Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2019/rec/949

University of Alberta
6.
Takebayashi, Satoshi.
Developments and Mechanistic Investigations of Ester, Imide,
and Ketone Hydrogenations.
Degree: PhD, Department of Chemistry, 2012, University of Alberta
URL: https://era.library.ualberta.ca/files/vh53ww99b
► The Noyori-type catalyst trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] (6) and its analogues are among the most active and enantioselective ketone hydrogenation systems reported to date. Its applications towards other…
(more)
▼ The Noyori-type catalyst
trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] (6) and its analogues are
among the most active and enantioselective ketone hydrogenation
systems reported to date. Its applications towards other types of
carbonyl compounds are, however, understudied. This dissertation
describes the first applications of this catalyst system towards
hydrogenations of esters and imides under mild reaction conditions.
Further, a detailed mechanistic study of this system is presented
using ketones, esters, and imides as substrates. The dihydride 6
was highly active towards the hydrogenation of esters.
Stoichiometric reactions between 6 and lactones proceeded at –80 °C
to form the net hydride insertion products, Ru-hemiacetaloxides.
The hemiacetaloxides were further hydrogenated at –40 °C under ~2
atm of H2 to form the corresponding Ru-alkoxides. Catalytic
hydrogenations could be carried out, even at –20 °C under 4 atm of
H2, however, these hydrogenations slowed over time due to
deactivation of the catalyst by primary alcohol products. The first
homogeneous monohydrogenation of imides was developed using 6 and
related compounds as catalysts. Further, upon optimization of
reaction conditions and imide structure, meso-cyclic imides were
desymmetrized in high ee via the monohydrogenation to form
kinetically unfavoured trans-hydroxy lactams with up to 5
stereogenic centres. Furthermore, the number of stereogenic centres
was increased from 5 to 7 using N-acyliminium ion chemistry. A
model for the origin of enantioselection was proposed using
substrate-catalyst steric interactions. Low temperature NMR studies
revealed that base catalyzes the rapid cis-trans isomerization to
form the thermodynamically more stable trans-isomer. It was
proposed that this rapid isomerization prevents racemization of a
product. Transition states for the formation of Ru-alkoxides from
addition between 6 and acetophenone were studied using an
intramolecular trapping experiment. Addition between 6 and
4-hydroxymethylacetophenone at –80 °C exclusively formed the net
hydride insertion product, Ru-secondary-alkoxide. Combined with
controlled experiments, this result is strong evidence for the
formation of a Ru–O interaction in the transition state, which
supports concerted formation of the Ru-alkoxides from 6 and
acetophenone.
Subjects/Keywords: imide; ketone; enantioselective; hydrogenation; ester
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Takebayashi, S. (2012). Developments and Mechanistic Investigations of Ester, Imide,
and Ketone Hydrogenations. (Doctoral Dissertation). University of Alberta. Retrieved from https://era.library.ualberta.ca/files/vh53ww99b
Chicago Manual of Style (16th Edition):
Takebayashi, Satoshi. “Developments and Mechanistic Investigations of Ester, Imide,
and Ketone Hydrogenations.” 2012. Doctoral Dissertation, University of Alberta. Accessed April 13, 2021.
https://era.library.ualberta.ca/files/vh53ww99b.
MLA Handbook (7th Edition):
Takebayashi, Satoshi. “Developments and Mechanistic Investigations of Ester, Imide,
and Ketone Hydrogenations.” 2012. Web. 13 Apr 2021.
Vancouver:
Takebayashi S. Developments and Mechanistic Investigations of Ester, Imide,
and Ketone Hydrogenations. [Internet] [Doctoral dissertation]. University of Alberta; 2012. [cited 2021 Apr 13].
Available from: https://era.library.ualberta.ca/files/vh53ww99b.
Council of Science Editors:
Takebayashi S. Developments and Mechanistic Investigations of Ester, Imide,
and Ketone Hydrogenations. [Doctoral Dissertation]. University of Alberta; 2012. Available from: https://era.library.ualberta.ca/files/vh53ww99b

University of Michigan
7.
Hopkins, Brett A.
Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions.
Degree: PhD, Chemistry, 2015, University of Michigan
URL: http://hdl.handle.net/2027.42/113418
► Enantiopure nitrogen and oxygen containing heterocycles are prominently displayed in a variety of important pharmaceuticals and biologically active products. As such accessing these scaffolds in…
(more)
▼ Enantiopure nitrogen and oxygen containing heterocycles are prominently displayed in a variety of important pharmaceuticals and biologically active products. As such accessing these scaffolds in an
enantioselective and efficient manner is an interesting challenge. We envisioned that novel asymmetric carboamination and carboetherification reactions would be powerful methods to synthesize these enantiopure heterocycles, as you can generate a library of enantiopure compounds in a facile manner with this approach. While these
enantioselective carboamination and carboetherification reactions are robust methods of accessing enantiopure heterocycles, at the onset of the work detailed in this thesis all of the efforts in this area were related to the formation of 5-membered rings bearing a single nitrogen heteroatom.
As such, this thesis entails the development of new
enantioselective carboamination and carboetherification reactions meant to address the above limitations. Chapter 2 details the development of an
enantioselective carboamination reaction to access enantiopure imidazolidin-2-ones in up to 97:3 er. This work also shows how reaction conditions, namely the choice of aryl halide, use of water additive and substrate electronics, affect the final enantioselectivity observed in the products. Chapter 3 details the development of a general procedure to access tetrahydroquinolines, tetrahydroisoquinolines and tetrahydroquinoxalines all in > 95:5 er. Furthermore, these reactions in chapter 3 are rare transformations of this type that allow for the synthesis of quaternary centers in high enantioselectivity. Chapter 4 details the
xiii
development of a novel carboetherification reaction, and how using a modular TADDOL ligand scaffold allowed us to rationally design a ligand that afforded our desired products in >95:5 er. Lastly, Chapter 5 entails the initial results looking into the synthesis of enantiopure benzofused oxygen heterocycles.
Advisors/Committee Members: Wolfe, John P. (committee member), Soellner, Matthew Bryan (committee member), McNeil, Anne Jennifer (committee member), Sanford, Melanie (committee member).
Subjects/Keywords: Enantioselective; Heterocycles; Chemistry; Science
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Hopkins, B. A. (2015). Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions. (Doctoral Dissertation). University of Michigan. Retrieved from http://hdl.handle.net/2027.42/113418
Chicago Manual of Style (16th Edition):
Hopkins, Brett A. “Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions.” 2015. Doctoral Dissertation, University of Michigan. Accessed April 13, 2021.
http://hdl.handle.net/2027.42/113418.
MLA Handbook (7th Edition):
Hopkins, Brett A. “Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions.” 2015. Web. 13 Apr 2021.
Vancouver:
Hopkins BA. Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions. [Internet] [Doctoral dissertation]. University of Michigan; 2015. [cited 2021 Apr 13].
Available from: http://hdl.handle.net/2027.42/113418.
Council of Science Editors:
Hopkins BA. Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions. [Doctoral Dissertation]. University of Michigan; 2015. Available from: http://hdl.handle.net/2027.42/113418

University of Hyderabad
8.
Rao, K Srinivasa.
Enantioselective Synthesis Of Terpenes; _.
Degree: chemisry, 1992, University of Hyderabad
URL: http://shodhganga.inflibnet.ac.in/handle/10603/25363
Available in chapter
References is given in chapter
Advisors/Committee Members: Mehta, Goverdhan.
Subjects/Keywords: Enantioselective; Synthesis
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APA (6th Edition):
Rao, K. S. (1992). Enantioselective Synthesis Of Terpenes; _. (Thesis). University of Hyderabad. Retrieved from http://shodhganga.inflibnet.ac.in/handle/10603/25363
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):
Rao, K Srinivasa. “Enantioselective Synthesis Of Terpenes; _.” 1992. Thesis, University of Hyderabad. Accessed April 13, 2021.
http://shodhganga.inflibnet.ac.in/handle/10603/25363.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Rao, K Srinivasa. “Enantioselective Synthesis Of Terpenes; _.” 1992. Web. 13 Apr 2021.
Vancouver:
Rao KS. Enantioselective Synthesis Of Terpenes; _. [Internet] [Thesis]. University of Hyderabad; 1992. [cited 2021 Apr 13].
Available from: http://shodhganga.inflibnet.ac.in/handle/10603/25363.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Rao KS. Enantioselective Synthesis Of Terpenes; _. [Thesis]. University of Hyderabad; 1992. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/25363
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Boston College
9.
Fager, Diana Catherine.
Catalytic Enantioselective Additions of Allyl Moieties to
α-Halomethyl Ketones, Trifluoromethyl Substituted NH-Ketimines, and
Nitriles.
Degree: PhD, Chemistry, 2020, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:108931
► Homoallylic alcohols and amines are commonly used building blocks for synthesis of biologically active molecules, yet a survey of the methods for their synthesis reveals…
(more)
▼ Homoallylic alcohols and amines are commonly used
building blocks for synthesis of biologically active molecules, yet
a survey of the methods for their synthesis reveals a plague of
limitations. Notably, the use of toxic reagents (Cr-, Mn-, and
Sn-containing), precious metal catalysts (Ir- and In-based),
non-ambient reaction temperatures (–78 to 140 °C), and extended
reaction times (up to 240 hours), limit application on larger
scale. The protection/deprotection sequences required to install
directing/activating groups for reaction efficiency and
enantioselectivity not only add synthetic steps but the conditions
required for removal of such entities are not amenable to more
complex and sensitive molecules. The development of catalytic
enantioselective methods for addition of allyl moieties to readily
available substrates including halomethyl ketones,
trifluoromethyl-substituted ketimines, and nitriles have been
developed. In the first two cases, an aminophenol-based boryl
catalyst is utilized for
enantioselective additions of allyl
moieties through transition states controlled by either
electrostatic attraction between a C–X bond and the catalyst’s
ammonium moiety or minimization of steric and dipolar repulsion. In
the latter, multicomponent additions to nitriles have been
developed for synthesis of cyclic amines. In all cases, application
is demonstrated through synthesis of otherwise difficult-to-access
derivatives or biologically active molecules.
Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).
Subjects/Keywords: allylation; aminophenol; crotylation; enantioselective; regioselective
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Fager, D. C. (2020). Catalytic Enantioselective Additions of Allyl Moieties to
α-Halomethyl Ketones, Trifluoromethyl Substituted NH-Ketimines, and
Nitriles. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:108931
Chicago Manual of Style (16th Edition):
Fager, Diana Catherine. “Catalytic Enantioselective Additions of Allyl Moieties to
α-Halomethyl Ketones, Trifluoromethyl Substituted NH-Ketimines, and
Nitriles.” 2020. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:108931.
MLA Handbook (7th Edition):
Fager, Diana Catherine. “Catalytic Enantioselective Additions of Allyl Moieties to
α-Halomethyl Ketones, Trifluoromethyl Substituted NH-Ketimines, and
Nitriles.” 2020. Web. 13 Apr 2021.
Vancouver:
Fager DC. Catalytic Enantioselective Additions of Allyl Moieties to
α-Halomethyl Ketones, Trifluoromethyl Substituted NH-Ketimines, and
Nitriles. [Internet] [Doctoral dissertation]. Boston College; 2020. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:108931.
Council of Science Editors:
Fager DC. Catalytic Enantioselective Additions of Allyl Moieties to
α-Halomethyl Ketones, Trifluoromethyl Substituted NH-Ketimines, and
Nitriles. [Doctoral Dissertation]. Boston College; 2020. Available from: http://dlib.bc.edu/islandora/object/bc-ir:108931

Boston College
10.
Alite, Hekla.
Kinetic Resolution of Alcohols by Catalytic Enantioselective
Sulfonylation and Silylation.
Degree: MS, Chemistry, 2012, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:101335
► Chapter 1: Brief overview of the catalytic enantioselective functionalization and kinetic resolution of alcohols Chapter 2: Kinetic resolution of syn-diols by catalytic enantioselective sulfonylation Chapter…
(more)
▼ Chapter 1: Brief overview of the catalytic
enantioselective functionalization and kinetic resolution of
alcohols Chapter 2: Kinetic resolution of syn-diols by catalytic
enantioselective sulfonylation Chapter 3: Significant improvement
on catalytic
enantioselective silylation of syn-diols and triols
through the use of a tetrazole additive
Advisors/Committee Members: Marc L. Snapper (Thesis advisor).
Subjects/Keywords: enantioselective; kinetic resolution; silylation; sulfonylation
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Alite, H. (2012). Kinetic Resolution of Alcohols by Catalytic Enantioselective
Sulfonylation and Silylation. (Masters Thesis). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101335
Chicago Manual of Style (16th Edition):
Alite, Hekla. “Kinetic Resolution of Alcohols by Catalytic Enantioselective
Sulfonylation and Silylation.” 2012. Masters Thesis, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:101335.
MLA Handbook (7th Edition):
Alite, Hekla. “Kinetic Resolution of Alcohols by Catalytic Enantioselective
Sulfonylation and Silylation.” 2012. Web. 13 Apr 2021.
Vancouver:
Alite H. Kinetic Resolution of Alcohols by Catalytic Enantioselective
Sulfonylation and Silylation. [Internet] [Masters thesis]. Boston College; 2012. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:101335.
Council of Science Editors:
Alite H. Kinetic Resolution of Alcohols by Catalytic Enantioselective
Sulfonylation and Silylation. [Masters Thesis]. Boston College; 2012. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101335

Boston College
11.
Radomkit, Suttipol.
New Concepts, Catalysts, and Methods for Enantioselective
Synthesis of C-B and C-C Bonds.
Degree: PhD, Chemistry, 2016, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:107272
► Chapter 1. Part A: N-Heterocyclic Carbenes Catalyzed Enantioselective Boryl Conjugate Additions to α,β-Unsaturated Ketones, Esters, Weinreb Amides and Aldehydes. The first broadly applicable enantioselective boryl…
(more)
▼ Chapter 1. Part A: N-Heterocyclic Carbenes Catalyzed
Enantioselective Boryl Conjugate Additions to α,β-Unsaturated
Ketones, Esters, Weinreb Amides and Aldehydes. The first broadly
applicable
enantioselective boryl conjugate addition reactions to a
variety of α,β-unsaturated carbonyls are reported. Transformations
are promoted by 5.0 mol % of a chiral Lewis basic N-heterocyclic
carbene. The distinctive feature of the reactions in
chemoselectivity of the method compared to the Cu-catalyzed
variants has been illustrated. Part B:
Enantioselective Synthesis
of Boron-Substituted Quaternary Carbon Stereogenic Centers through
N-Heterocyclic Carbenes Catalyzed Boryl Conjugate Additions to
Cyclic and Acyclic Enones The first examples of Lewis base
catalyzed
enantioselective boryl conjugate additions that afford
products containing boron-substituted quaternary carbon stereogenic
centers are presented. The carbon–boron bond forming reactions are
promoted by 1.0–5.0 mol % of a chiral N–hererocyclic carbene.
Cyclic or linear α,β–unsaturated ketones can be used as suitable
substrates and the desired products are obtained in 63–95% yield
and 91:9 to >99:1 enantiomeric ratio. The utility of the Lewis
base-catalyzed approach is demonstrated in the context of an
enantioselective formal synthesis of antifungal natural product
crassinervic acid. Chapter 2. Enantioselectivity Fluctuations in
Phosphine–Cu-Catalyzed
Enantioselective Boron-Allyl Addition to
Aryl-Substituted Olefins. Catalytic
enantioselective multicomponent
processes involving B2(pin)2, aryl or heteroaryl monosubstituted
olefins, and allylic phosphates or carbonates are disclosed.
Transformations promoted by a chiral Cu–phosphine complex afford
products that contain a primary C–B(pin) bond and an
allyl-substituted tertiary carbon stereogenic center in up to 84%
yield and 98:2 enantiomeric ratio. The utility of the approach is
showcased in the
enantioselective formal synthesis of biologically
active heliespirones A and C. Based on mechanistic and
computational studies, we show that enantioselectivities variations
can depend on electronic and/or steric factors of the alkene
substrate and the allyl electrophile as well as their
concentration. In most cases, selectivity loss can be minimized and
that the resulting insights are also applicable to reactions
involving Cu–H species. Chapter 3. Synthesis of Vicinal Diboronate
Compounds through Practical Phosphine–Copper Catalyzed
Three-Component Processes. The phosphine–Cu-catalyzed
multicomponent processes have been developed for a practical and
direct synthesis of vicinal diboronate compounds. Reactions of
alkenyl–boronates, allylic phosphates, and diboron reagents are
promoted by 2.5–10 mol % of a Cy3P–Cu complex affording a wide
range of desirable vicinal diboronate products. The ability for
easy access to either regioisomers of the products with a C–B(pin)
and an adjacent C–B(dan) bond that can be site-selectively
functionalized is a noteworthy feature of the method.
Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).
Subjects/Keywords: Boron; Carbon; Enantioselective Synthesis
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Radomkit, S. (2016). New Concepts, Catalysts, and Methods for Enantioselective
Synthesis of C-B and C-C Bonds. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:107272
Chicago Manual of Style (16th Edition):
Radomkit, Suttipol. “New Concepts, Catalysts, and Methods for Enantioselective
Synthesis of C-B and C-C Bonds.” 2016. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:107272.
MLA Handbook (7th Edition):
Radomkit, Suttipol. “New Concepts, Catalysts, and Methods for Enantioselective
Synthesis of C-B and C-C Bonds.” 2016. Web. 13 Apr 2021.
Vancouver:
Radomkit S. New Concepts, Catalysts, and Methods for Enantioselective
Synthesis of C-B and C-C Bonds. [Internet] [Doctoral dissertation]. Boston College; 2016. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:107272.
Council of Science Editors:
Radomkit S. New Concepts, Catalysts, and Methods for Enantioselective
Synthesis of C-B and C-C Bonds. [Doctoral Dissertation]. Boston College; 2016. Available from: http://dlib.bc.edu/islandora/object/bc-ir:107272

Boston College
12.
Moebius, David Charles.
Development of Sc(III)-catalyzed Homologation of Ketones by
Non-stabilized Diazomethanes.
Degree: PhD, Chemistry, 2011, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:101506
► The research of diazoalkanes dates back more than 100 years, yet a disproportionally small number of methods have been developed to utilize their unique reactivity…
(more)
▼ The research of diazoalkanes dates back more than 100
years, yet a disproportionally small number of methods have been
developed to utilize their unique reactivity patterns. This review
seeks to analyze the history of methods used to synthesize
diazoalkanes and to highlight the parallel growth in methods for
their use in carbonyl expansion reactions. The development of
Sc(III)-catalyzed ring expansion of cyclic ketones with
non-stabilized diazoalkanes is presented. A brief overview of
previous contributions to ring expansion methodology is presented
in order to provide appropriate context to newly discovered
methods. Our strategy for method development centered on several
issues of practicality with regard to efficient synthesis of diazo
nucleophiles as well as their safe handling. The results of this
initial discovery laid the groundwork for the development of the
first catalytic
enantioselective ring expansion of cyclic ketones
with diazoalkanes. As well as an improved methylene insertion
reaction of silyl-substituted diazomethanes.
Advisors/Committee Members: Jason S. Kingsbury (Thesis advisor).
Subjects/Keywords: catalysis; enantioselective; homologation; insertion; scandium
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Moebius, D. C. (2011). Development of Sc(III)-catalyzed Homologation of Ketones by
Non-stabilized Diazomethanes. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101506
Chicago Manual of Style (16th Edition):
Moebius, David Charles. “Development of Sc(III)-catalyzed Homologation of Ketones by
Non-stabilized Diazomethanes.” 2011. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:101506.
MLA Handbook (7th Edition):
Moebius, David Charles. “Development of Sc(III)-catalyzed Homologation of Ketones by
Non-stabilized Diazomethanes.” 2011. Web. 13 Apr 2021.
Vancouver:
Moebius DC. Development of Sc(III)-catalyzed Homologation of Ketones by
Non-stabilized Diazomethanes. [Internet] [Doctoral dissertation]. Boston College; 2011. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:101506.
Council of Science Editors:
Moebius DC. Development of Sc(III)-catalyzed Homologation of Ketones by
Non-stabilized Diazomethanes. [Doctoral Dissertation]. Boston College; 2011. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101506

Columbia University
13.
Gheewala, Chirag.
Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes.
Degree: 2017, Columbia University
URL: https://doi.org/10.7916/D8QN6K5N
► This thesis details the design and development of pentacarboxycyclopentadienes (PCCPs) as a new platform for enantioselective Brønsted acid catalysis. Prior to this research, enantioselective Brønsted…
(more)
▼ This thesis details the design and development of pentacarboxycyclopentadienes (PCCPs) as a new platform for enantioselective Brønsted acid catalysis. Prior to this research, enantioselective Brønsted acid catalysis was limited to the BINOL (and variations thereof) framework. While this catalyst platform has paved the way for a myriad of novel asymmetric chemical transformations, the utility of this catalyst scaffold has suffered from its lengthy and expensive preparations. As an alternative, starting from readily available 1,2,3,4,5-pentacarbomethoxycyclopentadiene and various chiral alcohols and amines, the synthesis of a library of strongly acidic chiral catalysts is described. The utility of these novel acid catalysts is explored in various transformations.
As a prelude to the heart of this work, Chapter 1 focuses on the advancements made in asymmetric Brønsted acid catalysis through BINOL-phosphate derived catalysts, focusing on the major accomplishments made by researchers since 2004. The provided review highlights the utility of these chiral acid catalysts but also reveals the need for a new scaffold that is more affordable and accessible.
Chapter 2 discusses the background of PCCPs, including its initial discovery and subsequent applications. Our work in developing novel transesterified and amidated derivatives is discussed with accompanying crystal structures of achiral and chiral PCCPs. pKa measurements demonstrate the capacity of PCCPs to be used as strong Brønsted acid catalysts and are compared to literature values of known Brønsted acid catalysts.
Chapter 3 focuses on the utility of PCCPs as enantioselective Brønsted acid catalysts in a variety of chemical transformations including the Mukaiyama-Mannich reaction, transfer hydrogenation, Pictet-Spengler reaction, diaryl alcohol substitution, Mukayaiama oxocarbenium aldol reaction, and [4+2]-cycloaddition. Catalyst loadings down to 0.01 mol% and reaction scale up to 25 grams in the Mukaiyama-Mannich reaction demonstrate the practical utility and robustness of PCCPs. Substrate scopes of these transformations show the breadth of accessible molecules that can be synthesized via PCCPs. Mechanistic rationales and transition state analyses are discussed in each of the transformations.
Subjects/Keywords: Chemistry; Chemistry, Organic; Enantioselective catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Gheewala, C. (2017). Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes. (Doctoral Dissertation). Columbia University. Retrieved from https://doi.org/10.7916/D8QN6K5N
Chicago Manual of Style (16th Edition):
Gheewala, Chirag. “Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes.” 2017. Doctoral Dissertation, Columbia University. Accessed April 13, 2021.
https://doi.org/10.7916/D8QN6K5N.
MLA Handbook (7th Edition):
Gheewala, Chirag. “Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes.” 2017. Web. 13 Apr 2021.
Vancouver:
Gheewala C. Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes. [Internet] [Doctoral dissertation]. Columbia University; 2017. [cited 2021 Apr 13].
Available from: https://doi.org/10.7916/D8QN6K5N.
Council of Science Editors:
Gheewala C. Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes. [Doctoral Dissertation]. Columbia University; 2017. Available from: https://doi.org/10.7916/D8QN6K5N

University of Manchester
14.
Page, Abigail.
Atropisomeric diaryl ethers and other non-biaryl atropisomers.
Degree: PhD, 2011, University of Manchester
URL: https://www.research.manchester.ac.uk/portal/en/theses/atropisomeric-diaryl-ethers-and-other-nonbiaryl-atropisomers(84281e1e-416b-4d2e-834b-1d215d6767cf).html
;
http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538368
► Atropisomerism is a property exhibited by molecules where rotation about one or more bonds is restricted. Along with biaryls, which are widely utilised in asymmetric…
(more)
▼ Atropisomerism is a property exhibited by molecules where rotation about one or more bonds is restricted. Along with biaryls, which are widely utilised in asymmetric catalysis, several other classes of compounds display atropisomerism. These molecules have applications in enantioselective synthesis, asymmetric catalysis and have been used to relay stereochemical information. There are, however, a number of challenges associated with their asymmetric synthesis (Chapter 1). This thesis describes research carried out on the synthesis and asymmetric synthesis of atropisomeric diaryl ethers. Chapter 2.1 explains how these ethers are synthesised in multi-gram quantities and to allow the incorporation of large ortho substituents. Having a number of diaryl ethers with suitable substitution patterns to achieve atropisomerism, Chapter 2.2 goes on to report two novel and complimentary biocatalytic approaches to the enantioselective synthesis of diaryl ethers by desymmetrisation. This chapter also describes a possible route towards the synthesis of a diaryl ether based ligand. Chapter 2.3 reports the lateral lithiation of meso diaryl ethers to yield diastereomeric atropisomers stereoselectively. Our attempts to use (-)-sparteine in lateral lithiations to desymmetrise a diaryl ether enantioselectively is also described. We go on to determine the configurational integrity of our organolithiums and the reaction pathway that exists in lithium substitution. Finally, the diastereoselective synthesis of both a diaryl ether (via a stereoselective reduction of a pro-chiral ketone) and a diaryl sulfide (via an addition reaction) is described in chapter 2.4. This chapter also reports the conformational behaviour of a diaryl amide in solution.
Subjects/Keywords: 547.1223; Atropisomer; enantioselective synthesis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Page, A. (2011). Atropisomeric diaryl ethers and other non-biaryl atropisomers. (Doctoral Dissertation). University of Manchester. Retrieved from https://www.research.manchester.ac.uk/portal/en/theses/atropisomeric-diaryl-ethers-and-other-nonbiaryl-atropisomers(84281e1e-416b-4d2e-834b-1d215d6767cf).html ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538368
Chicago Manual of Style (16th Edition):
Page, Abigail. “Atropisomeric diaryl ethers and other non-biaryl atropisomers.” 2011. Doctoral Dissertation, University of Manchester. Accessed April 13, 2021.
https://www.research.manchester.ac.uk/portal/en/theses/atropisomeric-diaryl-ethers-and-other-nonbiaryl-atropisomers(84281e1e-416b-4d2e-834b-1d215d6767cf).html ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538368.
MLA Handbook (7th Edition):
Page, Abigail. “Atropisomeric diaryl ethers and other non-biaryl atropisomers.” 2011. Web. 13 Apr 2021.
Vancouver:
Page A. Atropisomeric diaryl ethers and other non-biaryl atropisomers. [Internet] [Doctoral dissertation]. University of Manchester; 2011. [cited 2021 Apr 13].
Available from: https://www.research.manchester.ac.uk/portal/en/theses/atropisomeric-diaryl-ethers-and-other-nonbiaryl-atropisomers(84281e1e-416b-4d2e-834b-1d215d6767cf).html ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538368.
Council of Science Editors:
Page A. Atropisomeric diaryl ethers and other non-biaryl atropisomers. [Doctoral Dissertation]. University of Manchester; 2011. Available from: https://www.research.manchester.ac.uk/portal/en/theses/atropisomeric-diaryl-ethers-and-other-nonbiaryl-atropisomers(84281e1e-416b-4d2e-834b-1d215d6767cf).html ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538368

University of Edinburgh
15.
Roy, Iain David.
The development of novel enantioselective transition metal-catalysed 1,4- and 1,6-additions.
Degree: PhD, 2015, University of Edinburgh
URL: http://hdl.handle.net/1842/17921
► 1. ENANTIOSELECTIVE RHODIUM-CATALYSED 1,4-ARYLATION OF ALKENYLAZAARENES An extended study on the enantioselective rhodium-catalysed 1,4-arylation of alkenylazaarenes has been conducted. The 1,4-arylation of various alkenylazaarenes was…
(more)
▼ 1. ENANTIOSELECTIVE RHODIUM-CATALYSED 1,4-ARYLATION OF ALKENYLAZAARENES An extended study on the enantioselective rhodium-catalysed 1,4-arylation of alkenylazaarenes has been conducted. The 1,4-arylation of various alkenylazaarenes was performed with an extended range of arylboronic acids using a modified catalytic system with a superior chiral diene ligand. The result is the generation of a large number of b-stereocentre-containing azaarene compounds in high enantiopurity. Further studies also enabled the completion of a reactivity index between alkenylazaarenes and more traditional α,β-unsaturated carbonyl compounds and the incorporation of the arylation into arylation-aldol domino processes. 2. ENANTIOSELECTIVE RHODIUM-CATALYSED 1,4-ALKENYLATION OF ALKENYLAZAARENES An extensive study on the enantioselective rhodium-catalysed 1,4-alkenylation of alkenylazaarenes has been performed. Development of the reaction parameters identified novel heterogeneous reaction conditions in pure water with sub-stoichiometric SDS. Subsequent ligand development identified an anilide-based chiral diene that provided the best balance between conversion and enantiopurity. Using the novel conditions, a selection of alkenylazaarenes underwent enantioselective rhodium-catalysed 1,4-alkenylation with two alkenyl MIDA boronates to provide the alkenylation products in good to excellent yields and moderate to excellent enantioselectivities. 3. ENANTIOSELECTIVE COPPER-CATALYSED 1,6-BORATION OF ELECTRON-DEFICIENT DIENES The development of an enantioselective copper-catalysed 1,6-boration of electrondeficient dienes using B2(pin)2 has been achieved. The reactions provide chiral allylboronic esters that, after oxidation, result in secondary allylic alcohols in moderate to high yields with excellent enantioselectivities and 1,6:1,4-regioselectivities. The 1,6-borations proceed efficiently employing catalyst loadings as low as 0.0049 mol% and their scalability has been demonstrated up to 40.4 mmol. The methodology was applied to a concise synthesis of atorvastatin, in which the key 1,6-boration was performed using a catalyst loading of 0.02 mol%.
Subjects/Keywords: 541; enantioselective; transition metal
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Roy, I. D. (2015). The development of novel enantioselective transition metal-catalysed 1,4- and 1,6-additions. (Doctoral Dissertation). University of Edinburgh. Retrieved from http://hdl.handle.net/1842/17921
Chicago Manual of Style (16th Edition):
Roy, Iain David. “The development of novel enantioselective transition metal-catalysed 1,4- and 1,6-additions.” 2015. Doctoral Dissertation, University of Edinburgh. Accessed April 13, 2021.
http://hdl.handle.net/1842/17921.
MLA Handbook (7th Edition):
Roy, Iain David. “The development of novel enantioselective transition metal-catalysed 1,4- and 1,6-additions.” 2015. Web. 13 Apr 2021.
Vancouver:
Roy ID. The development of novel enantioselective transition metal-catalysed 1,4- and 1,6-additions. [Internet] [Doctoral dissertation]. University of Edinburgh; 2015. [cited 2021 Apr 13].
Available from: http://hdl.handle.net/1842/17921.
Council of Science Editors:
Roy ID. The development of novel enantioselective transition metal-catalysed 1,4- and 1,6-additions. [Doctoral Dissertation]. University of Edinburgh; 2015. Available from: http://hdl.handle.net/1842/17921

University of Edinburgh
16.
Hepburn, Hamish Bruce.
Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines.
Degree: PhD, 2015, University of Edinburgh
URL: http://hdl.handle.net/1842/17614
► A highly enantioselective and diastereoselective rhodium-catalysed addition of potassium allyltrifluoroborates to cyclic imines is described within. By utilising rhodium-chiral diene complexes, a wide range of…
(more)
▼ A highly enantioselective and diastereoselective rhodium-catalysed addition of potassium allyltrifluoroborates to cyclic imines is described within. By utilising rhodium-chiral diene complexes, a wide range of cyclic imines were successfully allylated in high yields and enantioselectivities. Using a variety of more highly substituted allyl reagents, additional stereocentres and further molecular complexity was achieved with good yields, enantioselectivities and diastereoselectivities. Investigations involving isomeric allyl species and deuterated allyl species provided results that gave mechanistic insight, leading to the proposal of a plausible mechanistic pathway and suggested the formation of interconverting allylrhodium intermediates. Furthermore, during these investigations, a highly interesting isomerisation of the allylrhodium intermediate was discovered. Such isomerisation led to the in situ formation of the more complex allylrhodium intermediates which led to complex products upon allylation with cyclic imines that would be difficult to synthesis via other methods. This isomerisation was found to occur for a range of cyclic imines and disubstituted allyltrifluoroborates, proceeding in good yields and diastereomeric ratios. Deuterium studies indicate it is probable that this isomerisation proceeds via a 1,4 rhodium migration and a plausible mechanism is proposed explaining both the connectivity of the products and the relative stereochemistry.
Subjects/Keywords: 546; rhodium; enantioselective; diene
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Chicago ·
MLA ·
Vancouver ·
CSE |
Export
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Manager
APA (6th Edition):
Hepburn, H. B. (2015). Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines. (Doctoral Dissertation). University of Edinburgh. Retrieved from http://hdl.handle.net/1842/17614
Chicago Manual of Style (16th Edition):
Hepburn, Hamish Bruce. “Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines.” 2015. Doctoral Dissertation, University of Edinburgh. Accessed April 13, 2021.
http://hdl.handle.net/1842/17614.
MLA Handbook (7th Edition):
Hepburn, Hamish Bruce. “Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines.” 2015. Web. 13 Apr 2021.
Vancouver:
Hepburn HB. Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines. [Internet] [Doctoral dissertation]. University of Edinburgh; 2015. [cited 2021 Apr 13].
Available from: http://hdl.handle.net/1842/17614.
Council of Science Editors:
Hepburn HB. Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines. [Doctoral Dissertation]. University of Edinburgh; 2015. Available from: http://hdl.handle.net/1842/17614

University of Illinois – Urbana-Champaign
17.
Roth, Aaron.
Stereoselective synthesis of 1,2-disubstitued βeta-amino alcohols and amino thiols.
Degree: PhD, Chemistry, 2020, University of Illinois – Urbana-Champaign
URL: http://hdl.handle.net/2142/108470
► This thesis covers the development and implementation of two distinct methodologies, both of which provide access to enantiomerically enriched, vicinally functionalized products. Chapter 1 provides…
(more)
▼ This thesis covers the development and implementation of two distinct methodologies, both of which provide access to enantiomerically enriched, vicinally functionalized products. Chapter 1 provides background and a brief introduction of the activation of Group 16 Lewis acids by Lewis bases. Chapter 2 details a method for the catalytic,
enantioselective, intermolecular, 1,2-sulfenoamination of alkenes. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. An expedited reaction optimization was achieved by employing multivariate Design of Experiment optimization ultimately resulting for a diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage. Chapter 3 of this thesis covers the identification of a method amenable to the rapid construction of diverse libraries of 1,2-amino alcohols. A number of methods are examined prior to the identification of 1,2-conjugate addition of aryl and alkyl lithium reagents to Ellman sulfonimines. The use of lithium reagents is key to overcome modest diastereoselectivity and poor reaction rates. A brief scope is explored and stereochemical models are discussed.
Advisors/Committee Members: Denmark, Scott E (advisor), Denmark, Scott E (Committee Chair), Sarlah, David (committee member), Hergenrother, Paul (committee member), Mehta, Angad (committee member).
Subjects/Keywords: Lewis base Catalysis; Stereoselective; Enantioselective
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
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APA (6th Edition):
Roth, A. (2020). Stereoselective synthesis of 1,2-disubstitued βeta-amino alcohols and amino thiols. (Doctoral Dissertation). University of Illinois – Urbana-Champaign. Retrieved from http://hdl.handle.net/2142/108470
Chicago Manual of Style (16th Edition):
Roth, Aaron. “Stereoselective synthesis of 1,2-disubstitued βeta-amino alcohols and amino thiols.” 2020. Doctoral Dissertation, University of Illinois – Urbana-Champaign. Accessed April 13, 2021.
http://hdl.handle.net/2142/108470.
MLA Handbook (7th Edition):
Roth, Aaron. “Stereoselective synthesis of 1,2-disubstitued βeta-amino alcohols and amino thiols.” 2020. Web. 13 Apr 2021.
Vancouver:
Roth A. Stereoselective synthesis of 1,2-disubstitued βeta-amino alcohols and amino thiols. [Internet] [Doctoral dissertation]. University of Illinois – Urbana-Champaign; 2020. [cited 2021 Apr 13].
Available from: http://hdl.handle.net/2142/108470.
Council of Science Editors:
Roth A. Stereoselective synthesis of 1,2-disubstitued βeta-amino alcohols and amino thiols. [Doctoral Dissertation]. University of Illinois – Urbana-Champaign; 2020. Available from: http://hdl.handle.net/2142/108470

University of Florida
18.
Mishra, Sourabh.
Facile Tuning of Atropisomeric P,N-Ligands towards Efficient Enantioselective Catalysis.
Degree: PhD, Chemistry, 2019, University of Florida
URL: https://ufdc.ufl.edu/UFE0052900
► Asymmetric catalysis is an important tool in the assembly of chiral compounds and the development of new chiral ligands is essential for efficient asymmetric induction.…
(more)
▼ Asymmetric catalysis is an important tool in the assembly of chiral compounds and the development of new chiral ligands is essential for efficient asymmetric induction. Over the past few decades, many chiral ligands have been developed, and a few outstanding ligands, such as Binol, Binap, Phox, etc. are now referred to as "privileged ligands." Axially chiral P,N-ligands, such as Quinap and Pinap, are well known for their unique reactivities and selectivities in various asymmetric transformations. To achieve high enantioselectivities in these asymmetric processes, ligand modification is typically required. Consequently, variations in 6-membered heterocycles were explored resulting in the development of Quinazolinap, Pyphos, and their analogues. However, the family of 6-membered heterocycles-based axially chiral ligands remains relatively small in comparison to Binap, Phox, and other privileged ligands, perhaps because low modularity of the 6-membered heterocycles has hindered the development of axially chiral P,N-ligands. However, 5-membered ring P,N-ligands such as Phox and Phim, though not axially chiral, have demonstrated high modularity. The recent advances in this field, challenges and the reactivity profiles of axially chiral P,N-ligands is summarized in Chapter 1.
Advisors/Committee Members: Aponick,Aaron (committee chair), Miller,Stephen Albert (committee member), Dolbier Jr,William R (committee member), James,Margaret O (committee member).
Subjects/Keywords: aponickgroup – catalysis – enantioselective – liganddesign – stackphos
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Mishra, S. (2019). Facile Tuning of Atropisomeric P,N-Ligands towards Efficient Enantioselective Catalysis. (Doctoral Dissertation). University of Florida. Retrieved from https://ufdc.ufl.edu/UFE0052900
Chicago Manual of Style (16th Edition):
Mishra, Sourabh. “Facile Tuning of Atropisomeric P,N-Ligands towards Efficient Enantioselective Catalysis.” 2019. Doctoral Dissertation, University of Florida. Accessed April 13, 2021.
https://ufdc.ufl.edu/UFE0052900.
MLA Handbook (7th Edition):
Mishra, Sourabh. “Facile Tuning of Atropisomeric P,N-Ligands towards Efficient Enantioselective Catalysis.” 2019. Web. 13 Apr 2021.
Vancouver:
Mishra S. Facile Tuning of Atropisomeric P,N-Ligands towards Efficient Enantioselective Catalysis. [Internet] [Doctoral dissertation]. University of Florida; 2019. [cited 2021 Apr 13].
Available from: https://ufdc.ufl.edu/UFE0052900.
Council of Science Editors:
Mishra S. Facile Tuning of Atropisomeric P,N-Ligands towards Efficient Enantioselective Catalysis. [Doctoral Dissertation]. University of Florida; 2019. Available from: https://ufdc.ufl.edu/UFE0052900

University of Oxford
19.
Thomas, Palacin.
Rapid synthesis of the Taxol core.
Degree: PhD, 2020, University of Oxford
URL: http://ora.ox.ac.uk/objects/uuid:e3e923a0-c1fb-4962-b03d-c58f95807f47
;
https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.800117
► This thesis describes the combination of prochiral/racemic electrophiles and non-stabilised nucleophiles in transition metal catalysed asymmetric transformations. The first part of the thesis focuses on…
(more)
▼ This thesis describes the combination of prochiral/racemic electrophiles and non-stabilised nucleophiles in transition metal catalysed asymmetric transformations. The first part of the thesis focuses on the synthetic approach towards the Taxol core, Taxadiene. The key steps involve a Cu-catalysed asymmetric conjugate addition (ACA) of alkylzirconocenes to enones and cyclisations. Three different routes towards the synthesis of Taxadiene were explored and investigations into the Cu-catalysed ACA led to the discovery of a novel domino hydrozirconation/conjugate addition/enolate trapping reaction. The second part of this thesis builds on the Rh-catalysed asymmetric coupling of boronic acids (vinyls, benzenes and heteroaromatics) and cyclic allyl chlorides, developed in the Fletcher group. Here, the main point is to couple a similar library of boronic acids to a more challenging electrophile, a racemic tetrahydropyridine (or N-heterocyclic piperidene) chloride, in order to access new chiral building blocks that can be found in a variety of natural products and their derivatives. The utility of this method is demonstrated by the total and formal asymmetric synthesis of the antipsychotic drug (-)-Preclamol. The last chapter builds on the Cu-catalysed asymmetric allylic alkylation of alkylzirconocenes to cyclic allyl chlorides, also developed in our group. The main goal of this work is once again to apply this methodology to the racemic N-heterocyclic piperidene chloride. Investigations led to the discovery of a kinetic resolution process which afforded novel 3-alkyl substituted tetrahydropyridines and enantioenriched 3-chloro-1,2,3,6-tetrahydropyridines in high enantioselectivities.
Subjects/Keywords: Total synthesis; Enantioselective catalysis
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Thomas, P. (2020). Rapid synthesis of the Taxol core. (Doctoral Dissertation). University of Oxford. Retrieved from http://ora.ox.ac.uk/objects/uuid:e3e923a0-c1fb-4962-b03d-c58f95807f47 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.800117
Chicago Manual of Style (16th Edition):
Thomas, Palacin. “Rapid synthesis of the Taxol core.” 2020. Doctoral Dissertation, University of Oxford. Accessed April 13, 2021.
http://ora.ox.ac.uk/objects/uuid:e3e923a0-c1fb-4962-b03d-c58f95807f47 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.800117.
MLA Handbook (7th Edition):
Thomas, Palacin. “Rapid synthesis of the Taxol core.” 2020. Web. 13 Apr 2021.
Vancouver:
Thomas P. Rapid synthesis of the Taxol core. [Internet] [Doctoral dissertation]. University of Oxford; 2020. [cited 2021 Apr 13].
Available from: http://ora.ox.ac.uk/objects/uuid:e3e923a0-c1fb-4962-b03d-c58f95807f47 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.800117.
Council of Science Editors:
Thomas P. Rapid synthesis of the Taxol core. [Doctoral Dissertation]. University of Oxford; 2020. Available from: http://ora.ox.ac.uk/objects/uuid:e3e923a0-c1fb-4962-b03d-c58f95807f47 ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.800117

Boston College
20.
van der Mei, Farid Willem.
Proton-Activated Catalysts for Efficient and Practical
Enantioselective Syntheses.
Degree: PhD, Chemistry, 2018, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:108140
► A previously developed catalytic system which can catalyze a variety of efficient and enantioselective allyl additions has been expanded to include regio-, diastereo-, Z-, and…
(more)
▼ A previously developed catalytic system which can
catalyze a variety of efficient and
enantioselective allyl
additions has been expanded to include regio-, diastereo-, Z-, and
enantioselective crotyl addition reactions. As discussed in Chapter
1, we were able to carry out efficient crotyl additions to
N-phosphinoyl imines by discovering a sufficiently Lewis acidic
co-catalyst, zinc(II) methoxide. This finding enabled us to vastly
improve reaction efficiency, in addition to enabling a
1,3-borotropic shift during the course of the reaction, turning a
previously α selective transformation into a γ-selective one. These
findings allowed us to develop a catalytic,
enantioselective crotyl
addition to N-phosphinoyl imines utilizing the commercially
available Z-crotyl–B(pin). When the reaction conditions elucidated
for crotyl additions to imines were utilized on a more
electrophilic substrate, such as trifluoromethyl ketones, an
entirely different finding was observed (Chapter 2). We found that
if direct addition is more facile than 1,3-borotropic shift the
transformation will again be α-selective, furnishing a linear
product, rather than the typically observed, branched crotyl
addition product. This finding allowed us to establish the first
broadly applicable, efficient, regio-, Z-, and
enantioselective
crotyl addition to trifluoromethyl ketones. We then highlighted the
utility of these products by using this method in tandem with
Z-selective olefin metathesis, affording complex, enantioenriched,
trifluoromethyl-containing homoallylic alcohols. During the course
of these studies, and through density functional theory
computations, we learned that Z- and E-crotyl–B(pin) react through
distinct transition states to form the same Z-olefin-containing
product with varying levels of enantioselectivity. These findings
led us to the results reported in Chapter 3, the first examples of
enantioselective aminophenol-promoted allyl additions to aldehydes.
We were able to utilize Z-CF3-allyl–B(pin) and Z-Cl-allyl–B(pin)
(both accessed through catalytic olefin metathesis) in Z- and
enantioselective additions to aldehydes, affording products which
cannot be accessed readily through previously reported methods. We
quickly realized the potential of Z-chloro-substituted homoallylic
alcohols for the synthesis of Z-homoallylic alcohols, to
demonstrate this potential, we carried out the total synthesis of
mycothiazole, which we accomplished in seven steps from
commercially available materials and 17% overall yield, a marked
improvement over the previous synthetic strategy.
Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).
Subjects/Keywords: Allylation; Aminophenol; Crotylation; Enantioselective; Regioselective
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
van der Mei, F. W. (2018). Proton-Activated Catalysts for Efficient and Practical
Enantioselective Syntheses. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:108140
Chicago Manual of Style (16th Edition):
van der Mei, Farid Willem. “Proton-Activated Catalysts for Efficient and Practical
Enantioselective Syntheses.” 2018. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:108140.
MLA Handbook (7th Edition):
van der Mei, Farid Willem. “Proton-Activated Catalysts for Efficient and Practical
Enantioselective Syntheses.” 2018. Web. 13 Apr 2021.
Vancouver:
van der Mei FW. Proton-Activated Catalysts for Efficient and Practical
Enantioselective Syntheses. [Internet] [Doctoral dissertation]. Boston College; 2018. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:108140.
Council of Science Editors:
van der Mei FW. Proton-Activated Catalysts for Efficient and Practical
Enantioselective Syntheses. [Doctoral Dissertation]. Boston College; 2018. Available from: http://dlib.bc.edu/islandora/object/bc-ir:108140

University of Alberta
21.
Hass, Michael J.
Reusable Ru and Rh catalysts for ester hydrogenations and
enyne cycloisomerizations.
Degree: MS, Department of Chemistry, 2012, University of Alberta
URL: https://era.library.ualberta.ca/files/n296x015t
► A method was developed to immobilize and reuse a catalyst for the asymmetric cycloisomerization of enynes. Immobilization is achieved through use of metal containing monomers,…
(more)
▼ A method was developed to immobilize and reuse a
catalyst for the asymmetric cycloisomerization of enynes.
Immobilization is achieved through use of metal containing
monomers, which are reacted with a cycloolefin via an alternating
ring-opening metathesis polymerization, assembling a
three-dimensional catalyst-organic framework. For example,
[RhCl((R)-5,5'-dinorimido BINAP)]2 was copolymerized with
ciscyclooctene using trans-RuCl2(CHPh)(PCy3)2 as a catalyst. After
supporting the resulting framework on barium sulphate, silver(I)
hexafluoroantimonate was added in the presence of enyne substrates
to generate cationic rhodium(I) sites. These catalytic rhodium(I)
sites catalyzed the asymmetric cycloisomerization of enynes, and
afforded a maximum of 620 turnovers and >99% ee over the
course of six runs. This catalyst was also used for batch reactions
with turnovers as high as 800. The maximum number of turnovers
reported in literature for a homogeneous non-tandem
cycloisomerization reaction is ten.
Subjects/Keywords: cycloisomerization; rhodium; catalyst immobilization; catalysis; enantioselective
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Hass, M. J. (2012). Reusable Ru and Rh catalysts for ester hydrogenations and
enyne cycloisomerizations. (Masters Thesis). University of Alberta. Retrieved from https://era.library.ualberta.ca/files/n296x015t
Chicago Manual of Style (16th Edition):
Hass, Michael J. “Reusable Ru and Rh catalysts for ester hydrogenations and
enyne cycloisomerizations.” 2012. Masters Thesis, University of Alberta. Accessed April 13, 2021.
https://era.library.ualberta.ca/files/n296x015t.
MLA Handbook (7th Edition):
Hass, Michael J. “Reusable Ru and Rh catalysts for ester hydrogenations and
enyne cycloisomerizations.” 2012. Web. 13 Apr 2021.
Vancouver:
Hass MJ. Reusable Ru and Rh catalysts for ester hydrogenations and
enyne cycloisomerizations. [Internet] [Masters thesis]. University of Alberta; 2012. [cited 2021 Apr 13].
Available from: https://era.library.ualberta.ca/files/n296x015t.
Council of Science Editors:
Hass MJ. Reusable Ru and Rh catalysts for ester hydrogenations and
enyne cycloisomerizations. [Masters Thesis]. University of Alberta; 2012. Available from: https://era.library.ualberta.ca/files/n296x015t

University of Alberta
22.
Sullivan, Erin Rae.
Enantioselective formation of propargylic alcohols.
Degree: PhD, Department of Chemistry, 2011, University of Alberta
URL: https://era.library.ualberta.ca/files/mk61rh89v
► Propargylic alcohol natural products are found in many species of terrestrial plants and marine organisms. Because these compounds are usually isolated from the natural source…
(more)
▼ Propargylic alcohol natural products are found in many
species of terrestrial plants and marine organisms. Because these
compounds are usually isolated from the natural source in only
small amounts, few studies of propargylic alcohol natural products
have been conducted to date. Nevertheless, these studies show
compounds with this backbone have diverse biological activities and
potential for pharmaceutical applications. Recently, routes have
been developed for the asymmetric addition of monoynes to
aldehydes, forming propargylic alcohols in high
enantioselectivities. At the commencement of this thesis research,
however, little work had been reported toward the asymmetric
addition of polyynes to aldehydes. As outlined in Chapter 1, the
polyynol functionality is quite prevalent in nature, and therefore
efficient synthetic routes to this framework could provide
compounds to help improve our understanding of the origin of their
diverse biological activities. Chapter 2 addresses the asymmetric
addition of terminal di- and triynes to aldehydes along, with a
one-pot Fritsch-Buttenberg-Wiechell rearrangement-asymmetric
addition reaction. The asymmetric addition of terminal diynes and
triynes would be a more direct route to polyynol natural products,
avoiding the use of tedious cross-coupling reactions. The one-pot
protocol would again be a more expedient route and would circumvent
the isolation of an unstable terminal polyyne. A second functional
group that has shown wide application in natural product synthesis
is the homoallylic propargylic alcohol moiety, as it contains three
distinct synthetic handles: the alkyne, alkene and alcohol. The
most direct route to a homoallylic propargylic alcohol is to
perform an allylation reaction on a propargylic aldehyde. The most
frequent allyl transfer method applied in natural product synthesis
is an allylation with an allylboron reagent known as an
allylboration reaction. Despite the popularity of this framework,
no catalytic asymmetric allylboration reaction currently exists for
propargylic aldehydes. Current methodologies to homoallylic
propargylic alcohols either apply a stoichiometric amount of a
chiral allylborane or the use of harsh allyl metal species. Chapter
3 describes the catalytic asymmetric allylboration of propargylic
aldehydes.
Subjects/Keywords: Alcohol; Polyyne; Enantioselective; natural product; Propargylic
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Sullivan, E. R. (2011). Enantioselective formation of propargylic alcohols. (Doctoral Dissertation). University of Alberta. Retrieved from https://era.library.ualberta.ca/files/mk61rh89v
Chicago Manual of Style (16th Edition):
Sullivan, Erin Rae. “Enantioselective formation of propargylic alcohols.” 2011. Doctoral Dissertation, University of Alberta. Accessed April 13, 2021.
https://era.library.ualberta.ca/files/mk61rh89v.
MLA Handbook (7th Edition):
Sullivan, Erin Rae. “Enantioselective formation of propargylic alcohols.” 2011. Web. 13 Apr 2021.
Vancouver:
Sullivan ER. Enantioselective formation of propargylic alcohols. [Internet] [Doctoral dissertation]. University of Alberta; 2011. [cited 2021 Apr 13].
Available from: https://era.library.ualberta.ca/files/mk61rh89v.
Council of Science Editors:
Sullivan ER. Enantioselective formation of propargylic alcohols. [Doctoral Dissertation]. University of Alberta; 2011. Available from: https://era.library.ualberta.ca/files/mk61rh89v

University of Utah
23.
Werner, Erik Winters.
Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts.
Degree: PhD, Chemistry, 2012, University of Utah
URL: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/1939/rec/684
► The Heck reaction is an important tool in target-directed syntheses, but its fullpotential has yet to be realized due to limited substrate compatibility. This limitationarises…
(more)
▼ The Heck reaction is an important tool in target-directed syntheses, but its fullpotential has yet to be realized due to limited substrate compatibility. This limitationarises from poor behavior of the selectivity-determining steps of migratory insertion and -hydride elimination when using electronically nonbiased substrates. The inability toaccommodate nonbiased alkenes is due to chemist's poor understanding of thecontrolling factors in these two key mechanistic steps. Herein are described Pd0 and PdIIcatalysts that exhibit unique selectivity in these electronically nonbiased molecularsystems.Chapter 1 describes the use of an electrophilic PdII catalyst to install two identicalaryl groups upon terminal aliphatic olefins. The use of the same system, with a differentaryl source, led to the discovery that electrophilic PdII catalysts are capable of selectivelydelivering (E)-styrenyl products from electronically nonbiased olefins.Chapter 2 details optimization of the PdII system to selectively delivertraditionally inaccessible (E)-styrenyl products, and evaluation of substrate scope.Mechanistic experiments are performed, suggesting that the unique selectivity observedis attributable to the cationic nature of the catalyst, that the ligand on Pd is required forcatalyst stability, and that the catalyst distinguishes between B-hydrogens on the basis ofC-H bond strength. These findings are applied to rational design of a Pd0-catalyzedHeck reaction of similar substrates.The Pd0-catalyzed system exhibits greater functional group tolerance than theoxidative system, is operationally simple, and requires no added stabilizing ligand. Thedesign and study of this reaction is the subject of Chapter 3. Mechanistic studies suggestthat solvent choice is crucial in allowing the metal center to distinguish between -hydrogens on the basis of their relative hydridic nature.The insight gained in the work described in Chapters 2 and 3 allowed for therational design of a system enabling enantioselective Heck reactions using acyclicsubstrates. This methodology, described in Chapter 4, was intended to deliver opticallyactive -aryl ketones from allylic alcohol substrates. After establishing that the reactionperforms as anticipated, it was applied to the unprecedented single-step enantioselectivesynthesis of y-aryl ketones, and aldehydes, and a d-aryl aldehyde.
Subjects/Keywords: Catalysis; Enantioselective; Heck; Palladium; Selective; Styrene
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Werner, E. W. (2012). Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts. (Doctoral Dissertation). University of Utah. Retrieved from http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/1939/rec/684
Chicago Manual of Style (16th Edition):
Werner, Erik Winters. “Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts.” 2012. Doctoral Dissertation, University of Utah. Accessed April 13, 2021.
http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/1939/rec/684.
MLA Handbook (7th Edition):
Werner, Erik Winters. “Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts.” 2012. Web. 13 Apr 2021.
Vancouver:
Werner EW. Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts. [Internet] [Doctoral dissertation]. University of Utah; 2012. [cited 2021 Apr 13].
Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/1939/rec/684.
Council of Science Editors:
Werner EW. Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts. [Doctoral Dissertation]. University of Utah; 2012. Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/1939/rec/684

Texas A&M University
24.
Lewis, Kyle.
The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis.
Degree: PhD, Chemistry, 2013, Texas A&M University
URL: http://hdl.handle.net/1969.1/151842
► Chiral-at-metal Werner complexes of the type (Λ/∆)-[Co(1,2-diamine)_(3)]^(3+) 3X^(–)have long been a cornerstone of coordination chemistry. However, despite being inexpensive and readily available in enantiopure form,…
(more)
▼ Chiral-at-metal Werner complexes of the type (Λ/∆)-[Co(1,2-diamine)_(3)]^(3+) 3X^(–)have long been a cornerstone of coordination chemistry. However, despite being inexpensive and readily available in enantiopure form, they have had no applications in
enantioselective organic synthesis. This derives from their poor solubility in organic solvents and the fact that the chelating ligands are non-labile, preventing metal based substrate activation. However, it was conceived that the abundant nitrogen-hydrogen bonds of the diamine ligands could activate Lewis basic substrates towards nucleophilic addition via hydrogen bonding.
Towards this end, the diastereomeric trications Λ-[Co((S,S)-dpen)_(3)]^(3+) and ∆-[Co((S,S)-dpen)_(3)]^(3+) (dpen = diphenyl ethylenediamine) were prepared by stereoselective syntheses. Incorporation of the lipophilic Bar_(f)^(–) (B(3,5-CF_(3)-C_(6)H_(3))_(4)^(–)) anion, among others, afforded the organic-soluble mixed salts Λ-[Co((S,S)-dpen)_(3)]^(3+) 2X^(–) BAr_(f)^(-) and ∆-[Co((S,S)-dpen)_(3)]^(3+) 2X^(–) Bar^( –)(X = Cl^(–), BF_(4)^(–), PF_(6)^(–)). These Werner complexes were then applied as hydrogen bond mediating catalysts for
enantioselective Michael additions of dialkyl malonates to nitroolefins.
The catalyzed Michael addition of dimethyl malonate (15a) to trans-β- nitrostyrene was optimized with respect to solvent, temperature, and catalyst counteranion and then extended to a range of nitroolefin substrates. Under optimized – conditions, Λ-(S,S)-3^(3+) 2BF_(4)^(–) Bar_(f)^(-) (10 mol%) catalyzes the Michael addition of 15a to 2-benzyloxy-trans-β-nitrostyrene in acetone at 0 °C in the presence of Et_(3)N (1.0 equiv) to afford dimethyl 2-(2-nitro-1-(2 benzyloxyphenyl)ethyl)malonate in 95% isolated yield and 96% ee.
This work marks the first time that a Werner-type complex has been applied as a catalyst for organic transformations with high enantioselectivities. The unique stereochemistry of the Werner complex, which features a chiral metal center, is primarily responsible for the stereoselectivity of the catalyzed reactions.
Advisors/Committee Members: Gladysz, John A (advisor), Darensbourg, Don (committee member), Wooley, Karen (committee member), Schwab, Arthur P (committee member).
Subjects/Keywords: Werner complex; hydrogen bonding; enantioselective; catalysis
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Chicago ·
MLA ·
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CSE |
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APA (6th Edition):
Lewis, K. (2013). The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis. (Doctoral Dissertation). Texas A&M University. Retrieved from http://hdl.handle.net/1969.1/151842
Chicago Manual of Style (16th Edition):
Lewis, Kyle. “The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis.” 2013. Doctoral Dissertation, Texas A&M University. Accessed April 13, 2021.
http://hdl.handle.net/1969.1/151842.
MLA Handbook (7th Edition):
Lewis, Kyle. “The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis.” 2013. Web. 13 Apr 2021.
Vancouver:
Lewis K. The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis. [Internet] [Doctoral dissertation]. Texas A&M University; 2013. [cited 2021 Apr 13].
Available from: http://hdl.handle.net/1969.1/151842.
Council of Science Editors:
Lewis K. The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis. [Doctoral Dissertation]. Texas A&M University; 2013. Available from: http://hdl.handle.net/1969.1/151842

Brigham Young University
25.
Walker, Whitney Kaye.
Electrophilic Catalysis Using Heterobimetallic Complexes.
Degree: PhD, 2017, Brigham Young University
URL: https://scholarsarchive.byu.edu/cgi/viewcontent.cgi?article=7962&context=etd
► Conventional ligand design in transition metal catalysis capitalizes on the ability of phosphorous, nitrogen, carbon, oxygen, and sulfur-based donors to modify the steric and electronic…
(more)
▼ Conventional ligand design in transition metal catalysis capitalizes on the ability of phosphorous, nitrogen, carbon, oxygen, and sulfur-based donors to modify the steric and electronic properties of a reactive metal center. Heterobimetallic transition metal complexes that contain a dative metal-metal bond provide a unique approach to ligand design where the reactivity of the metal center can be modified by metal-metal electronic communication. Our laboratory is interested in using the unique properties of heterobimetallic complexes to address significant limitations in current transition metal catalysis. My PhD work has focused on the ability of early/late transition metal heterobimetallic complexes to facilitate catalysis by speeding up reductive processes that occur at the late transition metal center. My initial studies were aimed at understanding the importance of the metal-metal interaction to catalysis in allylic amination reactions catalyzed by Pd–Ti heterobimetallic complexes and the potential of these catalysts to enable reactivity with challenging nitrogen nucleophiles. We also explored the substrate scope of the allylic amination with a variety of hindered amines and allylic chloride substrates under mild conditions. Aminations of this type have previously been shown to require harsh reaction conditions and tend to give low yields. A variety of sterically hindered secondary amine nucleophiles were able to readily undergo allylic substitution. Many of these aminations were complete within ten minutes. A series of allylic electrophiles were also shown to undergo the reaction. We have also looked at the ability of hindered amines to undergo intramolecular cyclizations to produce pyrrolidine and piperidine products. My continuing efforts in the laboratory are focused on developing chiral titanium-phosphinoamide ligands for enantioselective heterobimetallic catalysis. We have synthesized a series of chiral diamine-based phosphinoamide-titanium ligands in order to investigate enantioselective intramolecular aminations. Importantly, each of these new Ti-ligands enables room temperature catalysis in intramolecular aminations with hindered amines, suggesting contributions by the Ti center. Similar reactivity has not been achieved with monometallic chiral Pd catalysts in our lab. Importantly, many of these ligands enable modest enantioselectivity in the allylic aminations.
Subjects/Keywords: heterobimetallic; catalysis; allylic aminations; enantioselective; Chemistry
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
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APA (6th Edition):
Walker, W. K. (2017). Electrophilic Catalysis Using Heterobimetallic Complexes. (Doctoral Dissertation). Brigham Young University. Retrieved from https://scholarsarchive.byu.edu/cgi/viewcontent.cgi?article=7962&context=etd
Chicago Manual of Style (16th Edition):
Walker, Whitney Kaye. “Electrophilic Catalysis Using Heterobimetallic Complexes.” 2017. Doctoral Dissertation, Brigham Young University. Accessed April 13, 2021.
https://scholarsarchive.byu.edu/cgi/viewcontent.cgi?article=7962&context=etd.
MLA Handbook (7th Edition):
Walker, Whitney Kaye. “Electrophilic Catalysis Using Heterobimetallic Complexes.” 2017. Web. 13 Apr 2021.
Vancouver:
Walker WK. Electrophilic Catalysis Using Heterobimetallic Complexes. [Internet] [Doctoral dissertation]. Brigham Young University; 2017. [cited 2021 Apr 13].
Available from: https://scholarsarchive.byu.edu/cgi/viewcontent.cgi?article=7962&context=etd.
Council of Science Editors:
Walker WK. Electrophilic Catalysis Using Heterobimetallic Complexes. [Doctoral Dissertation]. Brigham Young University; 2017. Available from: https://scholarsarchive.byu.edu/cgi/viewcontent.cgi?article=7962&context=etd

Colorado State University
26.
Dalton, Derek M.
Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions.
Degree: PhD, Chemistry, 2013, Colorado State University
URL: http://hdl.handle.net/10217/80142
► Described herein are mechanistic studies and ligand development for Rh(I) catalyzed [2+2+2] cycloaddition reactions of alkene tethered isocyanates and exogenous alkynes. A mechanistic hypothesis has…
(more)
▼ Described herein are mechanistic studies and ligand development for Rh(I) catalyzed [2+2+2] cycloaddition reactions of alkene tethered isocyanates and exogenous alkynes. A mechanistic hypothesis has been proposed and supported through experiment. Novel perfluoroaryl Taddol phosphoramidite ligands were developed based on the mechanistic hypothesis. Improvements in product and enantioselectivity were found using the perfluoroaryl Taddol phosphoramidite ligand, CKphos. This catalyst system was studied by NMR, X-ray and DFT calculations. Rh(I)-C6F5 and Co(-1)-C6F5 interactions were found in the course of studying the CKphos catalysts. The Rh-CKphos catalyst system was used in the synthesis of the tricyclic core structure of the cylindricine and lepadiformine alkaloids. Finally a Zn(II)-catalyzed [4+2] cycloaddition of 1- azabutadienes and nitro olefins was discovered and developed as an efficient and selective means to synthesize tetrahydropyridines.
Advisors/Committee Members: Rovis, Tomislav (advisor), Wood, John L. (committee member), Kennan, Alan J. (committee member), Rappé, Anthony K. (committee member), Snow, Christopher D. (committee member).
Subjects/Keywords: cycloaddition; zinc; rhodium; enantioselective; heterocycles; catalysis
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
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APA (6th Edition):
Dalton, D. M. (2013). Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/80142
Chicago Manual of Style (16th Edition):
Dalton, Derek M. “Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions.” 2013. Doctoral Dissertation, Colorado State University. Accessed April 13, 2021.
http://hdl.handle.net/10217/80142.
MLA Handbook (7th Edition):
Dalton, Derek M. “Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions.” 2013. Web. 13 Apr 2021.
Vancouver:
Dalton DM. Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions. [Internet] [Doctoral dissertation]. Colorado State University; 2013. [cited 2021 Apr 13].
Available from: http://hdl.handle.net/10217/80142.
Council of Science Editors:
Dalton DM. Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions. [Doctoral Dissertation]. Colorado State University; 2013. Available from: http://hdl.handle.net/10217/80142

Boston College
27.
Edelstein, Emma Kate.
Enantioselective synthesis and stereospecific
transformations of organoboronic esters.
Degree: PhD, Chemistry, 2018, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:108038
► This dissertation details the development of several enantioselective or stereospecific transformations involving organoboronic esters. Chapter one will introduce electrophile-induced boronate rearrangements which underpins much of…
(more)
▼ This dissertation details the development of several
enantioselective or stereospecific transformations involving
organoboronic esters. Chapter one will introduce
electrophile-induced boronate rearrangements which underpins much
of the reactivity that will be discussed in subsequent chapters. In
chapter two the conjunctive cross-coupling reaction is presented.
Its development and application to the synthesis of non-racemic
boronic esters, along with its application to the synthesis of
enantioenriched allylic boronic esters, will be discussed. In
chapter three the cross-coupling of geminal bis(boronic) esters is
introduced and the development of a method to employ them in
cross-coupling with alkenyl bromides, affording enantioenriched
substituted allylic boronic esters is outlined. In chapter four we
highlight the utility of allylic boronic esters, and detail the
development of a cross-coupling reaction that involves the use of
these substrates and halide electrophiles to furnish
enantiomerically enriched products containing all carbon quaternary
stereocenters. Finally, in chapter five we describe the development
of a metalfree amination reaction of organoboron compounds, which
is able to deliver otherwise difficult-to-access enantiomerically
enriched α-tertiary amines.
Advisors/Committee Members: James P. Morken (Thesis advisor).
Subjects/Keywords: Boron; Catalysis; Cross-Coupling; Enantioselective; Palladium; Stereospecific
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Edelstein, E. K. (2018). Enantioselective synthesis and stereospecific
transformations of organoboronic esters. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:108038
Chicago Manual of Style (16th Edition):
Edelstein, Emma Kate. “Enantioselective synthesis and stereospecific
transformations of organoboronic esters.” 2018. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:108038.
MLA Handbook (7th Edition):
Edelstein, Emma Kate. “Enantioselective synthesis and stereospecific
transformations of organoboronic esters.” 2018. Web. 13 Apr 2021.
Vancouver:
Edelstein EK. Enantioselective synthesis and stereospecific
transformations of organoboronic esters. [Internet] [Doctoral dissertation]. Boston College; 2018. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:108038.
Council of Science Editors:
Edelstein EK. Enantioselective synthesis and stereospecific
transformations of organoboronic esters. [Doctoral Dissertation]. Boston College; 2018. Available from: http://dlib.bc.edu/islandora/object/bc-ir:108038

Boston College
28.
Wen, Fengqi.
Catalytic Enantioselective Tosylation of Meso-Alcohols with
an Amino-Acid-Based Small Molecule.
Degree: MS, Chemistry, 2011, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:101846
Chapter 1 Review of methodology developments in the
area of selective tosylation of alcohols. Chapter 2 Development of
a catalytic enantioselective tosylation of alcohols with an
amino-acid-based organocatalyst.
Advisors/Committee Members: Marc L. Snapper (Thesis advisor).
Subjects/Keywords: Catalytic; Enantioselective; Meso-Alcohols; Small Molecule; Tosylation
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Wen, F. (2011). Catalytic Enantioselective Tosylation of Meso-Alcohols with
an Amino-Acid-Based Small Molecule. (Masters Thesis). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101846
Chicago Manual of Style (16th Edition):
Wen, Fengqi. “Catalytic Enantioselective Tosylation of Meso-Alcohols with
an Amino-Acid-Based Small Molecule.” 2011. Masters Thesis, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:101846.
MLA Handbook (7th Edition):
Wen, Fengqi. “Catalytic Enantioselective Tosylation of Meso-Alcohols with
an Amino-Acid-Based Small Molecule.” 2011. Web. 13 Apr 2021.
Vancouver:
Wen F. Catalytic Enantioselective Tosylation of Meso-Alcohols with
an Amino-Acid-Based Small Molecule. [Internet] [Masters thesis]. Boston College; 2011. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:101846.
Council of Science Editors:
Wen F. Catalytic Enantioselective Tosylation of Meso-Alcohols with
an Amino-Acid-Based Small Molecule. [Masters Thesis]. Boston College; 2011. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101846

Boston College
29.
Eno, Meredith Suzanne.
Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond
Forming Reactions.
Degree: PhD, Chemistry, 2017, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:107422
► This dissertation describes the development of four metal-catalyzed carbon-carbon bond forming methods. The first project presented is a palladium-catalyzed proparyl-allyl cross-coupling which proceeds via a…
(more)
▼ This dissertation describes the development of four
metal-catalyzed carbon-carbon bond forming methods. The first
project presented is a palladium-catalyzed proparyl-allyl
cross-coupling which proceeds via a kinetic resolution to give
enantioenriched 1,5-enynes. Next the asymmetric rhodium-catalyzed
hydroformylation of 1-alkenes is described. This reaction delivers
synthetically useful a-chiral aldehydes in up to 98:2 er and up to
15:1 branched to linear ratio. The development of a unique
nickelcatalyzed asymmetric Kumada coupling of cyclic sulfates is
presented. Mechanistic studies reveal the reaction proceeds via an
SN2 oxidative addition of a chiral nickelcomplex. Finally,
a-Substituted allyl bis(boronic) esters, which are derived from
1,2-diboration of 1,3-dienes are shown to undergo allylation and
subsequent Suzuki coupling with aldehydes tethered to sp2
electrophiles. The carbocycle products obtained bear three
contiguous stereocenters and were used as intermediates in the
synthesis of complex molecules.
Advisors/Committee Members: James P. Morken (Thesis advisor).
Subjects/Keywords: catalysis; desymmetrization; diastereoselective; enantioselective; hydroformylation; metal
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APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Eno, M. S. (2017). Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond
Forming Reactions. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:107422
Chicago Manual of Style (16th Edition):
Eno, Meredith Suzanne. “Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond
Forming Reactions.” 2017. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:107422.
MLA Handbook (7th Edition):
Eno, Meredith Suzanne. “Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond
Forming Reactions.” 2017. Web. 13 Apr 2021.
Vancouver:
Eno MS. Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond
Forming Reactions. [Internet] [Doctoral dissertation]. Boston College; 2017. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:107422.
Council of Science Editors:
Eno MS. Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond
Forming Reactions. [Doctoral Dissertation]. Boston College; 2017. Available from: http://dlib.bc.edu/islandora/object/bc-ir:107422

Boston College
30.
Szymaniak, Adam Anthony.
Nonracemic Organoboronates by Transition Metal-Catalyzed C-C
and C-Si Bond Forming Reactions.
Degree: PhD, Chemistry, 2018, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:108119
► This dissertation will describe the development of three transition metal-catalyzed syntheses of nonracemic organoboronates. The first chapter explains the development of a palladium-catalyzed enantiotopic-group-selective cross-coupling…
(more)
▼ This dissertation will describe the development of
three transition metal-catalyzed syntheses of nonracemic
organoboronates. The first chapter explains the development of a
palladium-catalyzed enantiotopic-group-selective cross-coupling of
geminal bis(boronates) with alkenyl electrophiles. This process
enables the synthesis of highly valuable nonracemic disubstituted
allylic boronates. Chapter two describes a palladium-induced
1,2-metallate rearrangement of vinylboron “ate” complexes. The
newly developed process incorporates an alternative route for the
transmetallation step of Suzuki-Miyaura cross-couplings. Lastly, an
enantioselective platinum-catalyzed hydrosilylation of alkenyl
boronates is disclosed. This reaction enables the synthesis of
nonracemic geminal silylboronates for the divergent synthesis of
functionalized
Advisors/Committee Members: James P. Morken (Thesis advisor).
Subjects/Keywords: catalysis; enantioselective; nonracemic; organoboronates; palladium; platinum
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❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Szymaniak, A. A. (2018). Nonracemic Organoboronates by Transition Metal-Catalyzed C-C
and C-Si Bond Forming Reactions. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:108119
Chicago Manual of Style (16th Edition):
Szymaniak, Adam Anthony. “Nonracemic Organoboronates by Transition Metal-Catalyzed C-C
and C-Si Bond Forming Reactions.” 2018. Doctoral Dissertation, Boston College. Accessed April 13, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:108119.
MLA Handbook (7th Edition):
Szymaniak, Adam Anthony. “Nonracemic Organoboronates by Transition Metal-Catalyzed C-C
and C-Si Bond Forming Reactions.” 2018. Web. 13 Apr 2021.
Vancouver:
Szymaniak AA. Nonracemic Organoboronates by Transition Metal-Catalyzed C-C
and C-Si Bond Forming Reactions. [Internet] [Doctoral dissertation]. Boston College; 2018. [cited 2021 Apr 13].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:108119.
Council of Science Editors:
Szymaniak AA. Nonracemic Organoboronates by Transition Metal-Catalyzed C-C
and C-Si Bond Forming Reactions. [Doctoral Dissertation]. Boston College; 2018. Available from: http://dlib.bc.edu/islandora/object/bc-ir:108119
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