Synthesis of both Enantiomers of Hemiesters by Enantioselective Methanolysis of Meso Cyclic Anhydrides Catalyzed by α-Amino Acid-Derived Chiral Thioureas †
✍ Scribed by Manzano, Rubén; Andrés, José M.; Muruzábal, María-Dolores; Pedrosa, Rafael
- Book ID
- 127115720
- Publisher
- American Chemical Society
- Year
- 2010
- Tongue
- English
- Weight
- 780 KB
- Volume
- 75
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
Dedicated to Professor Ronald Breslow on the occasion of his 80th birthday Scheme 1. Chiral NHC- [11,12] or enzyme-catalyzed [13] intermolecular asymmetric Stetter reactions. EWG = electron-withdrawing group, Ar = aromatic group, Het = heteroaromatic group, R = rest. Scheme 2. Proposed reaction path
The chiral quaternary ammonium salt 1 serves as phase transfer catalyst for the enantioselective conversion of the glycine derivative 2 to a variety of cyclic and acyclic chiral oramino acids with enantioselectivities as high as 200:1 in alkylation and Michael addition reactions.