Cooperative coexistence: Effective interplay of two Bronsted acids in the asymmetric synthesis of isoquinuclidines

被引：165

作者：

Rueping, Magnus ^{[1
]}

Azap, Cengiz ^{[1
]}

机构：

[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 46期

关键词：

asymmetric synthesis; ion pairs; isoquinuclidines; Mannich bases; Michael addition;

D O I：

10.1002/anie.200603199

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Mannich-aza-Michael reaction in which both an electrophile and a nucleophile are activated provides a simple, highly enantioselective route to isoquinuclidines (1) from imines (2) and cyclohexenone (3). A feature of the reaction is the interplay of an achiral and a chiral Brønsted acid, which enable the asymmetric reaction process by cooperative activation of the enone and the imine. (Chemical Equation Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7832 / 7835

页数：4

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