A simple and highly effective water-compatible organocatalytic system for asymmetric direct Michael reactions of linear aldehydes to maleimides

被引：24

作者：

Qiao, Yupu ^{[1
]}

Headley, Allan D. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, Commerce, TX 75429 USA

来源：

GREEN CHEMISTRY | 2013年 / 15卷 / 10期

基金：

美国国家科学基金会;

关键词：

CARBON-CARBON BOND; ENANTIOSELECTIVE CONJUGATE ADDITION; AQUEOUS-MEDIA; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; ORGANIC-REACTIONS; RECYCLABLE ORGANOCATALYSTS; THIOUREA ORGANOCATALYST; PROTEASOME INHIBITOR; ALDOL REACTIONS; AMINO-ACIDS;

D O I：

10.1039/c3gc41024b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diarylprolinol silyl ether-based organocatalyst 2, in conjunction with ionic liquid supported (ILS) sulfonic acid 6a as co-catalyst, leads to a novel organocatalyst in aqueous media. The in situ generated catalyst demonstrated high reactivity and stereoselectivity for the Michael reactions of linear aldehydes to maleimides in brine without any organic solvents. For these reactions, up to 76% yield, 9:1 dr and 96% ee were obtained for a broad variety of aldehydes and maleimides.

引用

页码：2690 / 2694

页数：5

共 99 条

[1] Organocatalytic synthesis of optically active heteroaromatic compounds [J].