Organocatalytic Asymmetric Addition of Alcohols and Thiols to Activated Electrophiles: Efficient Dynamic Kinetic Resolution and Desymmetrization Protocols
Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine-, methionine-, and phenylalanine-...
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| Published in: | Journal of organic chemistry Vol. 73; no. 16; pp. 6409 - 6412 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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American Chemical Society
15-08-2008
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| Abstract | Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine-, methionine-, and phenylalanine-derived azalactones to undergo DKR with unprecedented levels of enantioselectivity using a synthetic catalyst. The first DKR of these substrates by thiols and the highly enantioselective desymmetrization of a meso-glutaric anhydride by thiolysis are also reported. |
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| AbstractList | Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine-, methionine-, and phenylalanine-derived azalactones to undergo DKR with unprecedented levels of enantioselectivity using a synthetic catalyst. The first DKR of these substrates by thiols and the highly enantioselective desymmetrization of a meso-glutaric anhydride by thiolysis are also reported. |
| Author | Gun’ko, Yuri K Peschiulli, Aldo Quigley, Cormac Tallon, Seán Connon, Stephen J |
| Author_xml | – sequence: 1 givenname: Aldo surname: Peschiulli fullname: Peschiulli, Aldo – sequence: 2 givenname: Cormac surname: Quigley fullname: Quigley, Cormac – sequence: 3 givenname: Seán surname: Tallon fullname: Tallon, Seán – sequence: 4 givenname: Yuri K surname: Gun’ko fullname: Gun’ko, Yuri K – sequence: 5 givenname: Stephen J surname: Connon fullname: Connon, Stephen J |
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| Keywords | Quinuclidine derivatives Enantioselectivity Nitrogen heterocycle Thiolysis Alcohol Oxygen heterocycle Organic sulfide Alkaloid Asymmetric synthesis Ureas Chemical synthesis Oxazole derivatives Electrophile Oxygen nitrogen heterocycle Alanine Thiol Phenylalanine Bifunctional compound Methionine Quinoline derivatives Steric hindrance Lactone Sulfur containing aminoacid α-Aminoacid Optical resolution Catalyst Nucleophile |
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| Snippet | Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile.... |
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| SubjectTerms | Alanine - analogs & derivatives Alanine - chemistry Alcohols - chemistry Aliphatic compounds Amino Acids - chemistry Anhydrides - chemistry Catalysis Catalysts: preparations and properties Chemistry Cinchona Alkaloids - chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Kinetics Lactones - chemistry Organic chemistry Preparations and properties Propanols - chemistry Sulfhydryl Compounds - chemistry Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Urea - analogs & derivatives Valine - analogs & derivatives |
| Title | Organocatalytic Asymmetric Addition of Alcohols and Thiols to Activated Electrophiles: Efficient Dynamic Kinetic Resolution and Desymmetrization Protocols |
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