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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