Asymmetric Mannich Reactions of β-Keto Esters with Acyl Imines Catalyzed by Cinchona Alkaloids
- 26 July 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (32) , 11256-11257
- https://doi.org/10.1021/ja0537373
Abstract
Cinchona alkaloids catalyze the enantioselective Mannich reaction of β-keto esters with acyl aryl imines. The reaction requires 10 mol % of cinchonine or cinchonidine. The reaction products are obtained in good yields (81−99%), high enantioselectivities (80−96% ee), and in diastereoselectivities that range from 1:1 to >95:5. The cinchonine-catalyzed reaction provides access to highly functionalized building blocks used in the asymmetric synthesis of a dihydropyrimidone and β-amino alcohol.Keywords
This publication has 28 references indexed in Scilit:
- Catalytic Enantioselective C−C Bond Forming Conjugate Additions with Vinyl SulfonesJournal of the American Chemical Society, 2005
- Direct Organocatalytic and Highly Enantio‐ and Diastereoselective Mannich Reactions of α‐Substituted α‐CyanoacetatesAngewandte Chemie International Edition in English, 2005
- A chiral molecular recognition approach to the formation of optically active quaternary centres in aza-Henry reactionsOrganic & Biomolecular Chemistry, 2005
- Catalytic Asymmetric Addition of β‐Ketoesters to Various Imines by Using Chiral Palladium ComplexesAngewandte Chemie International Edition in English, 2005
- Organocatalytic Enantioselective Conjugate Addition to AlkynonesJournal of the American Chemical Society, 2004
- Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic ActivationJournal of the American Chemical Society, 2004
- Synthetic Routes towards Enantiomerically Pure β‐Amino AcidsAngewandte Chemie International Edition in English, 2003
- Direct Catalytic Asymmetric Mannich Reactions of Malonates and β‐Keto EstersChemistry – A European Journal, 2003
- Catalytic Asymmetric Mannich Reactions of Glycine Derivatives with Imines. A New Approach to Optically Active α,β-Diamino Acid DerivativesThe Journal of Organic Chemistry, 2003
- Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected α-Amino Acid N-CarboxyanhydridesJournal of the American Chemical Society, 2001