Tandem catalytic asymmetric Friedel-Crafts/Henry reaction: Control of three contiguous acyclic stereocenters

被引：125

作者：

Arai, Takayoshi ^{[1
]}

Yokoyama, Naota ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Chiba 2638522, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 27期

关键词：

asymmetric catalysis; domino reactions; Friedel-Crafts reaction; Henry reaction; multicomponent reactions;

D O I：

10.1002/anie.200801373

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Good things come in threes: Highly functionalized indole derivatives with three contiguous stereocenters were formed in the title reaction of an indole, a nitroalkene, and an aldehyde with the imidazoline-aminophenol catalyst 1-CuOTf in the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The major isomers of the adducts were obtained with up to 99% ee. Tf = trifluoromethanesulfonyl, Ts = p-toluenesulfonyl; R = H, Me; R′,R″ = alkyl, aryl. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：4989 / 4992

页数：4

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