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
收藏
页码：2849 / 2853
页数：5
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