Highly Enantioselective Conjugate Addition-Cyclization Cascade Reaction of Malonates with o-Hydroxycinnamaldehydes: Asymmetric Synthesis of 4-Substituted Chromanols

被引：42

作者：

Lee, Yongcheon ^{[1
]}

Seo, Seung Woo ^{[1
]}

Kim, Sung-Gon ^{[1
]}

机构：

[1] Kyonggi Univ, Dept Chem, Suwon 443760, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 14-15期

基金：

新加坡国家研究基金会;

关键词：

asymmetric synthesis; chromans; conjugate addition; malonates; organocatalysts; ALPHA; BETA-UNSATURATED ALDEHYDES; ORGANOCATALYTIC REACTIONS; MICHAEL ADDITION; ANTIMICROBIAL ACTIVITY; ORGANOBORONIC ACIDS; IMINIUM ACTIVATION; CATALYSIS; DERIVATIVES; ACCESS; DIHYDROBENZOPYRANES;

D O I：

10.1002/adsc.201100324

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The asymmetric organocatalytic conjugate addition-cyclization reaction of malonates with o-hydroxycinnamaldehydes, which affords 4-substituted chroman-2-ols, has been established using a diphenylprolinol trimethylsilyl (TMS) ether as organocatalyst. The desired products were obtained with good to excellent yields and high enantioselectivities (up to >99% ee). Synthetically useful chroman derivatives were formed after subsequent reactions.

引用

收藏

页码：2671 / 2675

页数：5

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