Asymmetric Mannich Reactions of -Keto Esters with Acyl Imines Catalyzed by Cinchona Alkaloids
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- 作者：Sha Lou ; Brandon M. Taoka ; Amal Ting ; and Scott E. Schaus
- 刊名：Journal of the American Chemical Society
- 出版年：2005
- 出版时间：August 17, 2005
- 年：2005
- 卷：127
- 期：32
- 页码：11256 - 11257
- 全文大小：51K
- 年卷期：v.127,no.32(August 17, 2005)
- ISSN：1520-5126
文摘
Cinchona alkaloids catalyze the enantioselective Mannich reaction of 
-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 -amino alcohol.
-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 -amino alcohol.