Asymmetric Mannich reactions of β-keto esters with acyl imines catalyzed by cinchona alkaloids

被引：227

作者：

Lou, S

Taoka, BM

Ting, A

Schaus, SE

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

[2] Boston Univ, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 32期

关键词：

D O I：

10.1021/ja0537373

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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. Copyright © 2005 American Chemical Society.

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页码：11256 / 11257

页数：2

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