Asymmetric Michael Reaction of Acetaldehyde with Nitroolefins Catalyzed by Highly Water-Compatible Organocatalysts in Aqueous Media

被引：29

作者：

Qiao, Yupu ^{[1
]}

He, Junpeng ^{[1
]}

Ni, Bukuo ^{[1
]}

Headley, Allan D. ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 14-15期

关键词：

acetaldehyde; asymmetric synthesis; Michael reaction; water-compatible organocatalysts; ORGANIC-REACTIONS; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; CONJUGATE ADDITION; ALDOL REACTION; EFFICIENT ORGANOCATALYSTS; RECYCLABLE ORGANOCATALYST; IMINIUM ACTIVATION; MANNICH REACTION; ACID CATALYSTS; SOLVENT-FREE;

D O I：

10.1002/adsc.201200215

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel category of diarylprolinol silyl ether catalysts which contain different lengths of alkylamine tags, was designed and synthesized. These catalysts were used, along with benzoic acid as the co-catalyst, to catalyze the asymmetric Michael reaction of the highly reactive acetaldehyde with nitroolefins. For the reactions studied, this catalytic system exhibited high reactivity in brine without any organic solvents; good yields (3061%) and high enantioselectivities (8097% ee) for a wide variety of nitrostyrenes were obtained.

引用

页码：2849 / 2853

页数：5

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