Asymmetric Friedel-Crafts reaction of indoles with imines by an organic catalyst

被引：300

作者：

Wang, Yong-Qiang ^{[1
]}

Song, Jun ^{[1
]}

Hong, Ran ^{[1
]}

Li, Hongming ^{[1
]}

Deng, Li ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 25期

关键词：

D O I：

10.1021/ja062700v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this communication, we report an asymmetric Friedel-Crafts reaction of indoles with imines catalyzed by a bifunctional cinchona alkaloid catalyst. This is the first efficient organocatalytic asymmetric Friedel-Crafts reaction of indoles with imines. This reaction is operationally simple and, unprecedentedly, affords high enantioselectivity for a wide range of indoles and both aryl and alkyl imines. This establishes a direct, convergent, and versatile approach to optically active 3-indolyl methanamines, a structural motif embedded in numerous indole alkaloids and synthetic indole derivatives. Copyright © 2006 American Chemical Society.

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页码：8156 / 8157

页数：2

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