subject:(Enantioselective)

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 (6^th 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 (16^th 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 September 19, 2019. https://repository.library.brown.edu/studio/item/bdr:234/.

MLA Handbook (7^th Edition):

Wang, Sa. “Synthesis, Application, and Mechanistic Studies of the Asymmetric Addition of Organozinc Reagents to 3,4-Dihydroisoquinoline N-Oxide.” 2009. Web. 19 Sep 2019.

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 2019 Sep 19]. 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)

Subjects/Keywords: Enantioselective catalysis

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APA (6^th 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 (16^th Edition):

Zhang, Ping. “Enantioselective Catalysis Through 3,3'-reductive Elimination of Unsaturated Allyl Metal Complexes.” 2012. Doctoral Dissertation, Boston College. Accessed September 19, 2019. http://dlib.bc.edu/islandora/object/bc-ir:101159.

MLA Handbook (7^th Edition):

Zhang, Ping. “Enantioselective Catalysis Through 3,3'-reductive Elimination of Unsaturated Allyl Metal Complexes.” 2012. Web. 19 Sep 2019.

Vancouver:

Zhang P. Enantioselective Catalysis Through 3,3'-reductive Elimination of Unsaturated Allyl Metal Complexes. [Internet] [Doctoral dissertation]. Boston College; 2012. [cited 2019 Sep 19]. 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

University of Manchester

3. 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)

Subjects/Keywords: Atropisomer; enantioselective synthesis

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APA (6^th 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 (16^th Edition):

Page, Abigail. “Atropisomeric Diaryl Ethers and other Non-Biaryl Atropisomers.” 2011. Doctoral Dissertation, University of Manchester. Accessed September 19, 2019. http://www.manchester.ac.uk/escholar/uk-ac-man-scw:121988.

MLA Handbook (7^th Edition):

Page, Abigail. “Atropisomeric Diaryl Ethers and other Non-Biaryl Atropisomers.” 2011. Web. 19 Sep 2019.

Vancouver:

Page A. Atropisomeric Diaryl Ethers and other Non-Biaryl Atropisomers. [Internet] [Doctoral dissertation]. University of Manchester; 2011. [cited 2019 Sep 19]. 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

4. 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 (6^th 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 (16^th Edition):

Jensen, Katrina Helen. “Examination of catalyst and reactant electronic effects in enantioselective reactions.” 2010. Doctoral Dissertation, University of Utah. Accessed September 19, 2019. http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2019/rec/949.

MLA Handbook (7^th Edition):

Jensen, Katrina Helen. “Examination of catalyst and reactant electronic effects in enantioselective reactions.” 2010. Web. 19 Sep 2019.

Vancouver:

Jensen KH. Examination of catalyst and reactant electronic effects in enantioselective reactions. [Internet] [Doctoral dissertation]. University of Utah; 2010. [cited 2019 Sep 19]. 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

5. 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 (6^th 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 (16^th Edition):

Takebayashi, Satoshi. “Developments and Mechanistic Investigations of Ester, Imide, and Ketone Hydrogenations.” 2012. Doctoral Dissertation, University of Alberta. Accessed September 19, 2019. https://era.library.ualberta.ca/files/vh53ww99b.

MLA Handbook (7^th Edition):

Takebayashi, Satoshi. “Developments and Mechanistic Investigations of Ester, Imide, and Ketone Hydrogenations.” 2012. Web. 19 Sep 2019.

Vancouver:

Takebayashi S. Developments and Mechanistic Investigations of Ester, Imide, and Ketone Hydrogenations. [Internet] [Doctoral dissertation]. University of Alberta; 2012. [cited 2019 Sep 19]. 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 Hyderabad

6. 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 (6^th 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 (16^th Edition):

Rao, K Srinivasa. “Enantioselective Synthesis Of Terpenes; _.” 1992. Thesis, University of Hyderabad. Accessed September 19, 2019. 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 (7^th Edition):

Rao, K Srinivasa. “Enantioselective Synthesis Of Terpenes; _.” 1992. Web. 19 Sep 2019.

Vancouver:

Rao KS. Enantioselective Synthesis Of Terpenes; _. [Internet] [Thesis]. University of Hyderabad; 1992. [cited 2019 Sep 19]. 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

University of Manchester

7. 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)

Subjects/Keywords: 547.1223; Atropisomer; enantioselective synthesis

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APA (6^th 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 (16^th Edition):

Page, Abigail. “Atropisomeric diaryl ethers and other non-biaryl atropisomers.” 2011. Doctoral Dissertation, University of Manchester. Accessed September 19, 2019. 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 (7^th Edition):

Page, Abigail. “Atropisomeric diaryl ethers and other non-biaryl atropisomers.” 2011. Web. 19 Sep 2019.

Vancouver:

Page A. Atropisomeric diaryl ethers and other non-biaryl atropisomers. [Internet] [Doctoral dissertation]. University of Manchester; 2011. [cited 2019 Sep 19]. 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

Boston College

8. 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 (6^th 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 (16^th Edition):

Radomkit, Suttipol. “New Concepts, Catalysts, and Methods for Enantioselective Synthesis of C-B and C-C Bonds.” 2016. Doctoral Dissertation, Boston College. Accessed September 19, 2019. http://dlib.bc.edu/islandora/object/bc-ir:107272.

MLA Handbook (7^th Edition):

Radomkit, Suttipol. “New Concepts, Catalysts, and Methods for Enantioselective Synthesis of C-B and C-C Bonds.” 2016. Web. 19 Sep 2019.

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 2019 Sep 19]. 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

University of Edinburgh

9. 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)

Subjects/Keywords: 546; rhodium; enantioselective; diene

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th 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 (16^th Edition):

Hepburn, Hamish Bruce. “Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines.” 2015. Doctoral Dissertation, University of Edinburgh. Accessed September 19, 2019. http://hdl.handle.net/1842/17614.

MLA Handbook (7^th Edition):

Hepburn, Hamish Bruce. “Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines.” 2015. Web. 19 Sep 2019.

Vancouver:

Hepburn HB. Enantioselective rhodium-catalysed nucleophilic allylation of cyclic imines. [Internet] [Doctoral dissertation]. University of Edinburgh; 2015. [cited 2019 Sep 19]. 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 Edinburgh

10. 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 (6^th 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 (16^th 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 September 19, 2019. http://hdl.handle.net/1842/17921.

MLA Handbook (7^th Edition):

Roy, Iain David. “The development of novel enantioselective transition metal-catalysed 1,4- and 1,6-additions.” 2015. Web. 19 Sep 2019.

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 2019 Sep 19]. 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

Columbia University

11. 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 (6^th 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 (16^th Edition):

Gheewala, Chirag. “Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes.” 2017. Doctoral Dissertation, Columbia University. Accessed September 19, 2019. https://doi.org/10.7916/D8QN6K5N.

MLA Handbook (7^th Edition):

Gheewala, Chirag. “Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes.” 2017. Web. 19 Sep 2019.

Vancouver:

Gheewala C. Enantioselective Brønsted Acid Catalysis with Chiral Pentacarboxycyclopentadienes. [Internet] [Doctoral dissertation]. Columbia University; 2017. [cited 2019 Sep 19]. 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

Boston College

12. 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)

Subjects/Keywords: enantioselective; kinetic resolution; silylation; sulfonylation

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APA (6^th 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 (16^th Edition):

Alite, Hekla. “Kinetic Resolution of Alcohols by Catalytic Enantioselective Sulfonylation and Silylation.” 2012. Masters Thesis, Boston College. Accessed September 19, 2019. http://dlib.bc.edu/islandora/object/bc-ir:101335.

MLA Handbook (7^th Edition):

Alite, Hekla. “Kinetic Resolution of Alcohols by Catalytic Enantioselective Sulfonylation and Silylation.” 2012. Web. 19 Sep 2019.

Vancouver:

Alite H. Kinetic Resolution of Alcohols by Catalytic Enantioselective Sulfonylation and Silylation. [Internet] [Masters thesis]. Boston College; 2012. [cited 2019 Sep 19]. 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

13. 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)

Subjects/Keywords: catalysis; enantioselective; homologation; insertion; scandium

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APA (6^th 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 (16^th Edition):

Moebius, David Charles. “Development of Sc(III)-catalyzed Homologation of Ketones by Non-stabilized Diazomethanes.” 2011. Doctoral Dissertation, Boston College. Accessed September 19, 2019. http://dlib.bc.edu/islandora/object/bc-ir:101506.

MLA Handbook (7^th Edition):

Moebius, David Charles. “Development of Sc(III)-catalyzed Homologation of Ketones by Non-stabilized Diazomethanes.” 2011. Web. 19 Sep 2019.

Vancouver:

Moebius DC. Development of Sc(III)-catalyzed Homologation of Ketones by Non-stabilized Diazomethanes. [Internet] [Doctoral dissertation]. Boston College; 2011. [cited 2019 Sep 19]. 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

University of Michigan

14. 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 (6^th 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 (16^th Edition):

Hopkins, Brett A. “Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions.” 2015. Doctoral Dissertation, University of Michigan. Accessed September 19, 2019. http://hdl.handle.net/2027.42/113418.

MLA Handbook (7^th Edition):

Hopkins, Brett A. “Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions.” 2015. Web. 19 Sep 2019.

Vancouver:

Hopkins BA. Enantioselective Synthesis of Heterocycles via Palladium Catalyzed Alkene Difunctionalization Reactions. [Internet] [Doctoral dissertation]. University of Michigan; 2015. [cited 2019 Sep 19]. 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

Rutgers University

15. Li, Le, 1980-. Development of catalytic enantioselective Aldol, Mannich, Friedlaender reactions.

Degree: PhD, Chemistry and Chemical Biology, 2010, Rutgers University

URL: http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056483

►

In Chapter I, I introduce the explosive development of enantioselective organocatalysis. Selected significant landmarks in this area are reviewed and highlighted in this chapter. Chapter… (more)

Subjects/Keywords: Enantioselective catalysis; Diamino amino acids

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APA (6^th Edition):

Li, Le, 1. (2010). Development of catalytic enantioselective Aldol, Mannich, Friedlaender reactions. (Doctoral Dissertation). Rutgers University. Retrieved from http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056483

Chicago Manual of Style (16^th Edition):

Li, Le, 1980-. “Development of catalytic enantioselective Aldol, Mannich, Friedlaender reactions.” 2010. Doctoral Dissertation, Rutgers University. Accessed September 19, 2019. http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056483.

MLA Handbook (7^th Edition):

Li, Le, 1980-. “Development of catalytic enantioselective Aldol, Mannich, Friedlaender reactions.” 2010. Web. 19 Sep 2019.

Vancouver:

Li, Le 1. Development of catalytic enantioselective Aldol, Mannich, Friedlaender reactions. [Internet] [Doctoral dissertation]. Rutgers University; 2010. [cited 2019 Sep 19]. Available from: http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056483.

Council of Science Editors:

Li, Le 1. Development of catalytic enantioselective Aldol, Mannich, Friedlaender reactions. [Doctoral Dissertation]. Rutgers University; 2010. Available from: http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056483

University of Georgia

16. Baird, Suzanne Elizabeth. Enantioselective toxicity, bioaccumulation, and biotransformation of fipronil in fathead minnows (Pimephales promelas).

Degree: MS, Toxicology, 2009, University of Georgia

URL: http://purl.galileo.usg.edu/uga_etd/baird_suzanne_e_200912_ms

► Fipronil is a relatively new chiral, phenylpyrazole insecticide used to control both agricultural and household invertebrate pests. Fipronil is applied as a racemate, or equal… (more)

Subjects/Keywords: Acute Toxicity; Subchronic Toxicity; Pesticides; Chiral; Enantioselective

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APA (6^th Edition):

Baird, S. E. (2009). Enantioselective toxicity, bioaccumulation, and biotransformation of fipronil in fathead minnows (Pimephales promelas). (Masters Thesis). University of Georgia. Retrieved from http://purl.galileo.usg.edu/uga_etd/baird_suzanne_e_200912_ms

Chicago Manual of Style (16^th Edition):

Baird, Suzanne Elizabeth. “Enantioselective toxicity, bioaccumulation, and biotransformation of fipronil in fathead minnows (Pimephales promelas).” 2009. Masters Thesis, University of Georgia. Accessed September 19, 2019. http://purl.galileo.usg.edu/uga_etd/baird_suzanne_e_200912_ms.

MLA Handbook (7^th Edition):

Baird, Suzanne Elizabeth. “Enantioselective toxicity, bioaccumulation, and biotransformation of fipronil in fathead minnows (Pimephales promelas).” 2009. Web. 19 Sep 2019.

Vancouver:

Baird SE. Enantioselective toxicity, bioaccumulation, and biotransformation of fipronil in fathead minnows (Pimephales promelas). [Internet] [Masters thesis]. University of Georgia; 2009. [cited 2019 Sep 19]. Available from: http://purl.galileo.usg.edu/uga_etd/baird_suzanne_e_200912_ms.

Council of Science Editors:

Baird SE. Enantioselective toxicity, bioaccumulation, and biotransformation of fipronil in fathead minnows (Pimephales promelas). [Masters Thesis]. University of Georgia; 2009. Available from: http://purl.galileo.usg.edu/uga_etd/baird_suzanne_e_200912_ms

University of Utah

17. 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 (6^th 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 (16^th Edition):

Werner, Erik Winters. “Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts.” 2012. Doctoral Dissertation, University of Utah. Accessed September 19, 2019. http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/1939/rec/684.

MLA Handbook (7^th Edition):

Werner, Erik Winters. “Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts.” 2012. Web. 19 Sep 2019.

Vancouver:

Werner EW. Development and evaluation of reactions utilizing uniquely selective electrophilic Pd catalysts. [Internet] [Doctoral dissertation]. University of Utah; 2012. [cited 2019 Sep 19]. 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

18. Lewis, Kyle. The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis.

Degree: 2013, Texas A&M University

URL: http://hdl.handle.net/1969.1/151842

► Chiral-at-metal Werner complexes of the type (?/?)-[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 (?/?)-[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 ?-[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 ?-[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-?- nitrostyrene was optimized with respect to solvent, temperature, and catalyst counteranion and then extended to a range of nitroolefin substrates. Under optimized ? conditions, ?-(S,S)-3^(3+) 2BF_(4)^(?) Bar_(f)^(-) (10 mol%) catalyzes the Michael addition of 15a to 2-benzyloxy-trans-?-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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APA (6^th Edition):

Lewis, K. (2013). The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis. (Thesis). Texas A&M University. Retrieved from http://hdl.handle.net/1969.1/151842

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Lewis, Kyle. “The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis.” 2013. Thesis, Texas A&M University. Accessed September 19, 2019. http://hdl.handle.net/1969.1/151842.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Lewis, Kyle. “The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis.” 2013. Web. 19 Sep 2019.

Vancouver:

Lewis K. The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis. [Internet] [Thesis]. Texas A&M University; 2013. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/1969.1/151842.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Lewis K. The Development of Werner-type Cobalt Complexes in Enantioselective Hydrogen Bond Mediated Catalysis. [Thesis]. Texas A&M University; 2013. Available from: http://hdl.handle.net/1969.1/151842

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Alberta

19. 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)

Subjects/Keywords: cycloisomerization; rhodium; catalyst immobilization; catalysis; enantioselective

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APA (6^th 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 (16^th Edition):

Hass, Michael J. “Reusable Ru and Rh catalysts for ester hydrogenations and enyne cycloisomerizations.” 2012. Masters Thesis, University of Alberta. Accessed September 19, 2019. https://era.library.ualberta.ca/files/n296x015t.

MLA Handbook (7^th Edition):

Hass, Michael J. “Reusable Ru and Rh catalysts for ester hydrogenations and enyne cycloisomerizations.” 2012. Web. 19 Sep 2019.

Vancouver:

Hass MJ. Reusable Ru and Rh catalysts for ester hydrogenations and enyne cycloisomerizations. [Internet] [Masters thesis]. University of Alberta; 2012. [cited 2019 Sep 19]. 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

20. 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 (6^th 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 (16^th Edition):

Sullivan, Erin Rae. “Enantioselective formation of propargylic alcohols.” 2011. Doctoral Dissertation, University of Alberta. Accessed September 19, 2019. https://era.library.ualberta.ca/files/mk61rh89v.

MLA Handbook (7^th Edition):

Sullivan, Erin Rae. “Enantioselective formation of propargylic alcohols.” 2011. Web. 19 Sep 2019.

Vancouver:

Sullivan ER. Enantioselective formation of propargylic alcohols. [Internet] [Doctoral dissertation]. University of Alberta; 2011. [cited 2019 Sep 19]. 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 Sydney

21. Bromhead, Liam Joseph. Enantioselective Synthesis of Strigolactone Analogues .

Degree: 2016, University of Sydney

URL: http://hdl.handle.net/2123/16114

► On the instigation of A/Prof C. S. P. McErlean I have investigated asymmetric approaches for the synthesis of strigolactone analogues. Strigolactones are an emergent class… (more)

Subjects/Keywords: Chemistry; Organic; Catalysis; Enantioselective; Strigolactone; Synthesis

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APA (6^th Edition):

Bromhead, L. J. (2016). Enantioselective Synthesis of Strigolactone Analogues . (Thesis). University of Sydney. Retrieved from http://hdl.handle.net/2123/16114

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Bromhead, Liam Joseph. “Enantioselective Synthesis of Strigolactone Analogues .” 2016. Thesis, University of Sydney. Accessed September 19, 2019. http://hdl.handle.net/2123/16114.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Bromhead, Liam Joseph. “Enantioselective Synthesis of Strigolactone Analogues .” 2016. Web. 19 Sep 2019.

Vancouver:

Bromhead LJ. Enantioselective Synthesis of Strigolactone Analogues . [Internet] [Thesis]. University of Sydney; 2016. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/2123/16114.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Bromhead LJ. Enantioselective Synthesis of Strigolactone Analogues . [Thesis]. University of Sydney; 2016. Available from: http://hdl.handle.net/2123/16114

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Manchester

22. Rae, James. Copper-catalysed silicon and boron functionalisation of heterocycles and allenes.

Degree: 2015, University of Manchester

URL: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:269795

► Silicon holds a privileged position in organic chemistry as the carbon-silicon bond can be utilised in many important transformations. As such, developing practical and efficient… (more)

Subjects/Keywords: Copper; Enantioselective; Silicon; Boron; Catalysis; Allene

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APA (6^th Edition):

Rae, J. (2015). Copper-catalysed silicon and boron functionalisation of heterocycles and allenes. (Doctoral Dissertation). University of Manchester. Retrieved from http://www.manchester.ac.uk/escholar/uk-ac-man-scw:269795

Chicago Manual of Style (16^th Edition):

Rae, James. “Copper-catalysed silicon and boron functionalisation of heterocycles and allenes.” 2015. Doctoral Dissertation, University of Manchester. Accessed September 19, 2019. http://www.manchester.ac.uk/escholar/uk-ac-man-scw:269795.

MLA Handbook (7^th Edition):

Rae, James. “Copper-catalysed silicon and boron functionalisation of heterocycles and allenes.” 2015. Web. 19 Sep 2019.

Vancouver:

Rae J. Copper-catalysed silicon and boron functionalisation of heterocycles and allenes. [Internet] [Doctoral dissertation]. University of Manchester; 2015. [cited 2019 Sep 19]. Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:269795.

Council of Science Editors:

Rae J. Copper-catalysed silicon and boron functionalisation of heterocycles and allenes. [Doctoral Dissertation]. University of Manchester; 2015. Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:269795

Clemson University

23. Hall, April. Sorption and Enantiomerization of Current Use Chiral Pesticides.

Degree: PhD, Environmental Engineering and Earth Science, 2012, Clemson University

URL: https://tigerprints.clemson.edu/all_dissertations/1046

► Chiral pesticides are prevalent in the environment today and are known to react selectively with chiral environmental components such as microbes, enzymes, and other… (more)

▼ Chiral pesticides are prevalent in the environment today and are known to react selectively with chiral environmental components such as microbes, enzymes, and other naturally occurring chiral materials. In addition, chiral sorption is a process that has been occasionally investigated in the study of homochirality (the exclusive presence of one enantiomer in living organisms), but almost overlooked in environmental science. For chiral sorption to occur, the sorbent and sorbate must be chiral entities. In the environment, there are abundant natural surfaces that are chiral, including clay minerals and organic matter present in soil, sediment and aqueous solution. A knowledge of isomerization, including the special case of enantiomerization, of chiral pesticides is also crucial in understanding the fate of these chiral pollutants, especially for pesticides marketed as a 'chiral switch':, i.e. formulations containing only or mostly the active enantiomer. The goal of this research was to provide more insight into sorption and enantiomerization of chiral pesticides in the presence of mineral surfaces. Sorption experiments with malathion and metalaxyl and selected minerals, along with their individual enantiomers, were conducted and results analyzed by achiral and chiral high performance liquid chromatography (HPLC). Investigation with racemic malathion resulted in significant sorption to all sorbents, with the exception of the negligible sorption to kaolinite. Sorption was fit to the Freundlich model, with n2hr > 1 for bentonite, calcite, and montmorillonite while the biotic solids diatomaceous earth and seashells had n2hr < 1. KF,2hr values indicated decreasing sorption capacity in the order montmorillonite, bentonite, calcite, seashells, and diatomaceous earth. Chiral analysis indicated nonenantioselective sorption for malathion, which exhibited racemic enantiomeric fractions (EFs) for all sorbents. Sorption of the individual enantiomers of malathion, R-(+)- and S-(-)-malathion, resulted in enantiomerization to racemic EFs after contact with the mineral sorbents. Adding malathion enantiomers to minerals and analyzing the aqueous phase after 15 min of centrifugation resulted in enantiomerization to racemic EF values for R-(+)-malathion, but only partial enantiomerization of S-(-)-malathion. Malathion enantiomers also decreased or increased in EF for controls containing either only water or â-cyclodextrin, but enantiomerization to the racemate was not complete after two hours. It was hypothesized that malathion is undergoing proton exchange with the mineral surfaces causing enantiomerization. Construction of sorption isotherms revealed that the racemate and enantiomers have different isotherm shapes, possibly indicating different sorption mechanisms. Sorption was fit to the Freundlich model, with n2hr being statistically different for the racemate and S-(-)-malathion and R-(+)- and S-(-)-malathion with bentonite, but not for calcite and montmorillonite. KF,2hr values were not… Advisors/Committee Members: Lee, Cindy M, Elzerman , Alan W, Freedman , David L, Garrison , Arthur W.

Subjects/Keywords: chiral; enantiomerization; enantioselective; pesticides; sorption; Environmental Sciences

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APA (6^th Edition):

Hall, A. (2012). Sorption and Enantiomerization of Current Use Chiral Pesticides. (Doctoral Dissertation). Clemson University. Retrieved from https://tigerprints.clemson.edu/all_dissertations/1046

Chicago Manual of Style (16^th Edition):

Hall, April. “Sorption and Enantiomerization of Current Use Chiral Pesticides.” 2012. Doctoral Dissertation, Clemson University. Accessed September 19, 2019. https://tigerprints.clemson.edu/all_dissertations/1046.

MLA Handbook (7^th Edition):

Hall, April. “Sorption and Enantiomerization of Current Use Chiral Pesticides.” 2012. Web. 19 Sep 2019.

Vancouver:

Hall A. Sorption and Enantiomerization of Current Use Chiral Pesticides. [Internet] [Doctoral dissertation]. Clemson University; 2012. [cited 2019 Sep 19]. Available from: https://tigerprints.clemson.edu/all_dissertations/1046.

Council of Science Editors:

Hall A. Sorption and Enantiomerization of Current Use Chiral Pesticides. [Doctoral Dissertation]. Clemson University; 2012. Available from: https://tigerprints.clemson.edu/all_dissertations/1046

University of Illinois – Urbana-Champaign

24. Chi, Hyungmin. Lewis base catalyzed enantioselective sulfenoamination of alkenes.

Degree: PhD, Chemistry, 2016, University of Illinois – Urbana-Champaign

URL: http://hdl.handle.net/2142/95503

► The concept of Lewis base activation of Lewis acid has been successfully applied to the enantioselective sulfenoamination of olefins. The unreactive, achiral Lewis acidic sulfenylating… (more)

Subjects/Keywords: Sulfenoamination; Enantioselective catalysis; Lewis base; Negative catalysis

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APA (6^th Edition):

Chi, H. (2016). Lewis base catalyzed enantioselective sulfenoamination of alkenes. (Doctoral Dissertation). University of Illinois – Urbana-Champaign. Retrieved from http://hdl.handle.net/2142/95503

Chicago Manual of Style (16^th Edition):

Chi, Hyungmin. “Lewis base catalyzed enantioselective sulfenoamination of alkenes.” 2016. Doctoral Dissertation, University of Illinois – Urbana-Champaign. Accessed September 19, 2019. http://hdl.handle.net/2142/95503.

MLA Handbook (7^th Edition):

Chi, Hyungmin. “Lewis base catalyzed enantioselective sulfenoamination of alkenes.” 2016. Web. 19 Sep 2019.

Vancouver:

Chi H. Lewis base catalyzed enantioselective sulfenoamination of alkenes. [Internet] [Doctoral dissertation]. University of Illinois – Urbana-Champaign; 2016. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/2142/95503.

Council of Science Editors:

Chi H. Lewis base catalyzed enantioselective sulfenoamination of alkenes. [Doctoral Dissertation]. University of Illinois – Urbana-Champaign; 2016. Available from: http://hdl.handle.net/2142/95503

Princeton University

25. Welin, Eric Robert. New Concepts in Catalysis: The Development of Photoredox Catalysis as a Powerful Synthetic Tool .

Degree: PhD, 2015, Princeton University

URL: http://arks.princeton.edu/ark:/88435/dsp011831cn340

► In the last half-century few developments have changed the chemical community more than the development of novel forms of catalysis. As a result of the… (more)

Subjects/Keywords: Catalysis; Enantioselective; Organic Chemistry; Organocatalysis; Photoredox; Synthesis

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APA (6^th Edition):

Welin, E. R. (2015). New Concepts in Catalysis: The Development of Photoredox Catalysis as a Powerful Synthetic Tool . (Doctoral Dissertation). Princeton University. Retrieved from http://arks.princeton.edu/ark:/88435/dsp011831cn340

Chicago Manual of Style (16^th Edition):

Welin, Eric Robert. “New Concepts in Catalysis: The Development of Photoredox Catalysis as a Powerful Synthetic Tool .” 2015. Doctoral Dissertation, Princeton University. Accessed September 19, 2019. http://arks.princeton.edu/ark:/88435/dsp011831cn340.

MLA Handbook (7^th Edition):

Welin, Eric Robert. “New Concepts in Catalysis: The Development of Photoredox Catalysis as a Powerful Synthetic Tool .” 2015. Web. 19 Sep 2019.

Vancouver:

Welin ER. New Concepts in Catalysis: The Development of Photoredox Catalysis as a Powerful Synthetic Tool . [Internet] [Doctoral dissertation]. Princeton University; 2015. [cited 2019 Sep 19]. Available from: http://arks.princeton.edu/ark:/88435/dsp011831cn340.

Council of Science Editors:

Welin ER. New Concepts in Catalysis: The Development of Photoredox Catalysis as a Powerful Synthetic Tool . [Doctoral Dissertation]. Princeton University; 2015. Available from: http://arks.princeton.edu/ark:/88435/dsp011831cn340

University of Edinburgh

26. Wieczysty, Martin David. C-H functionalisation of 2-aryl cyclic 1,3-dicarbonyl compounds ; Enantioselective Rh(I)-catalysed cyclisation of arylboron compounds onto ketones.

Degree: PhD, 2015, University of Edinburgh

URL: http://hdl.handle.net/1842/18741

► 1. C–H Functionalisation of 2 Aryl Cyclic 1,3-Dicarbonyl Compounds Two enolate-directed C–H functionalisation protocols have been developed using 2-aryl cyclic 1,3-dicarbonyl compounds as substrates. Reactions… (more)

Subjects/Keywords: 547; organic chemistry; C–H functionalisation; enantioselective

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APA (6^th Edition):

Wieczysty, M. D. (2015). C-H functionalisation of 2-aryl cyclic 1,3-dicarbonyl compounds ; Enantioselective Rh(I)-catalysed cyclisation of arylboron compounds onto ketones. (Doctoral Dissertation). University of Edinburgh. Retrieved from http://hdl.handle.net/1842/18741

Chicago Manual of Style (16^th Edition):

Wieczysty, Martin David. “C-H functionalisation of 2-aryl cyclic 1,3-dicarbonyl compounds ; Enantioselective Rh(I)-catalysed cyclisation of arylboron compounds onto ketones.” 2015. Doctoral Dissertation, University of Edinburgh. Accessed September 19, 2019. http://hdl.handle.net/1842/18741.

MLA Handbook (7^th Edition):

Wieczysty, Martin David. “C-H functionalisation of 2-aryl cyclic 1,3-dicarbonyl compounds ; Enantioselective Rh(I)-catalysed cyclisation of arylboron compounds onto ketones.” 2015. Web. 19 Sep 2019.

Vancouver:

Wieczysty MD. C-H functionalisation of 2-aryl cyclic 1,3-dicarbonyl compounds ; Enantioselective Rh(I)-catalysed cyclisation of arylboron compounds onto ketones. [Internet] [Doctoral dissertation]. University of Edinburgh; 2015. [cited 2019 Sep 19]. Available from: http://hdl.handle.net/1842/18741.

Council of Science Editors:

Wieczysty MD. C-H functionalisation of 2-aryl cyclic 1,3-dicarbonyl compounds ; Enantioselective Rh(I)-catalysed cyclisation of arylboron compounds onto ketones. [Doctoral Dissertation]. University of Edinburgh; 2015. Available from: http://hdl.handle.net/1842/18741

University of New South Wales

27. Wang, Lili. Enantiospecific fate of polycyclic musks in biological wastewater treatment processes and the environment.

Degree: Civil & Environmental Engineering, 2014, University of New South Wales

URL: http://handle.unsw.edu.au/1959.4/54122 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:13165/SOURCE02?view=true

► Enantiospecific wastewater and environmental fates of chiral synthetic polycyclic musks (PCMs) including galaxolide (HHCB), tonalide (AHTN), phantolide (AHDI), traseolide (ATII) and cashmeran (DBMI) were investigated.… (more)

▼ Enantiospecific wastewater and environmental fates of chiral synthetic polycyclic musks (PCMs) including galaxolide (HHCB), tonalide (AHTN), phantolide (AHDI), traseolide (ATII) and cashmeran (DBMI) were investigated. These PCMs are commonly used ingredients in personal care products (PCPs) and household detergents.A sensitive and robust enantioselective analytical method based on gas chromatography with tandem mass spectrometry (GC–MS/MS) was developed to facilitate enantiospecific measurement of PCMs. The analysis of individual PCM enantiomers enabled the calculation and comparison of enantiomeric fractions (EFs) among various sample matrices.PCM concentrations and EFs were determined in a range of household products in order to assess source water compositions to sewage treatment plants. PCM concentrations and EFs were then monitored in wastewater treatment plant (WWTP) influent and effluent, and a range of landfill leachates. No significant changes in EF were observed in WWTP samples or leachate samples. This indicated that any biodegradative processes were not significantly enantioselective.The enantiospecific fate of PCMs was further assessed in a laboratory scale anaerobic membrane bioreactor (AnMBR). While the AnMBR was observed to be effective for the removal of PCMs by a combination of biodegradation and biosorption, negligible change in EF was observed. Again, this indicated that the dominant biodegradation pathways were not appreciably enantioselective.Finally, alternative means of biodegradation/transformation were investigated using fungi and the enzymes that they produce. Experiments were undertaken with fungal batch reactions, as well as semi-continuous treatment with a sequencing batch fungal reactor. In both cases, some significant changes to EF were observed. Monitoring of EF in both cases provided insights to the mechanisms of removal of PCMs, which would otherwise not have been available. Observed changes in EF confirmed a role for biotransformation among the removal mechanisms and facilitated the diagnosis of reducing sequencing batch reactor performance over time. This work has enhanced our understanding of the fate of chiral PCMs in various matrices. Observed changes in EFs revealed the potential for using EF as a powerful tool to distinguish between biological and physical processes in some wastewater treatment processes, which in turn offer opportunities to improve the operation and management of these systems. Advisors/Committee Members: Khan, Stuart, Civil & Environmental Engineering, Faculty of Engineering, UNSW, Stuetz, Richard, Civil & Environmental Engineering, Faculty of Engineering, UNSW.

Subjects/Keywords: Enantioselective analysis; Enantiomeric fraction; Polycyclic musks

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APA (6^th Edition):

Wang, L. (2014). Enantiospecific fate of polycyclic musks in biological wastewater treatment processes and the environment. (Doctoral Dissertation). University of New South Wales. Retrieved from http://handle.unsw.edu.au/1959.4/54122 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:13165/SOURCE02?view=true

Chicago Manual of Style (16^th Edition):

Wang, Lili. “Enantiospecific fate of polycyclic musks in biological wastewater treatment processes and the environment.” 2014. Doctoral Dissertation, University of New South Wales. Accessed September 19, 2019. http://handle.unsw.edu.au/1959.4/54122 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:13165/SOURCE02?view=true.

MLA Handbook (7^th Edition):

Wang, Lili. “Enantiospecific fate of polycyclic musks in biological wastewater treatment processes and the environment.” 2014. Web. 19 Sep 2019.

Vancouver:

Wang L. Enantiospecific fate of polycyclic musks in biological wastewater treatment processes and the environment. [Internet] [Doctoral dissertation]. University of New South Wales; 2014. [cited 2019 Sep 19]. Available from: http://handle.unsw.edu.au/1959.4/54122 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:13165/SOURCE02?view=true.

Council of Science Editors:

Wang L. Enantiospecific fate of polycyclic musks in biological wastewater treatment processes and the environment. [Doctoral Dissertation]. University of New South Wales; 2014. Available from: http://handle.unsw.edu.au/1959.4/54122 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:13165/SOURCE02?view=true

Boston College

28. 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)

Subjects/Keywords: Boron; Catalysis; Cross-Coupling; Enantioselective; Palladium; Stereospecific

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APA (6^th 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 (16^th Edition):

Edelstein, Emma Kate. “Enantioselective synthesis and stereospecific transformations of organoboronic esters.” 2018. Doctoral Dissertation, Boston College. Accessed September 19, 2019. http://dlib.bc.edu/islandora/object/bc-ir:108038.

MLA Handbook (7^th Edition):

Edelstein, Emma Kate. “Enantioselective synthesis and stereospecific transformations of organoboronic esters.” 2018. Web. 19 Sep 2019.

Vancouver:

Edelstein EK. Enantioselective synthesis and stereospecific transformations of organoboronic esters. [Internet] [Doctoral dissertation]. Boston College; 2018. [cited 2019 Sep 19]. 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

29. 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 (6^th 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 (16^th Edition):

Wen, Fengqi. “Catalytic Enantioselective Tosylation of Meso-Alcohols with an Amino-Acid-Based Small Molecule.” 2011. Masters Thesis, Boston College. Accessed September 19, 2019. http://dlib.bc.edu/islandora/object/bc-ir:101846.

MLA Handbook (7^th Edition):

Wen, Fengqi. “Catalytic Enantioselective Tosylation of Meso-Alcohols with an Amino-Acid-Based Small Molecule.” 2011. Web. 19 Sep 2019.

Vancouver:

Wen F. Catalytic Enantioselective Tosylation of Meso-Alcohols with an Amino-Acid-Based Small Molecule. [Internet] [Masters thesis]. Boston College; 2011. [cited 2019 Sep 19]. 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

30. 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)

Subjects/Keywords: catalysis; desymmetrization; diastereoselective; enantioselective; hydroformylation; metal

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APA (6^th 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 (16^th Edition):

Eno, Meredith Suzanne. “Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond Forming Reactions.” 2017. Doctoral Dissertation, Boston College. Accessed September 19, 2019. http://dlib.bc.edu/islandora/object/bc-ir:107422.

MLA Handbook (7^th Edition):

Eno, Meredith Suzanne. “Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond Forming Reactions.” 2017. Web. 19 Sep 2019.

Vancouver:

Eno MS. Development of Metal-Catalyzed Asymmetric Carbon-Carbon Bond Forming Reactions. [Internet] [Doctoral dissertation]. Boston College; 2017. [cited 2019 Sep 19]. 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

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Open Access Theses and Dissertations