Direct organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes

被引：126

作者：

Sundén, H ^{[1
]}

Ibrahem, I ^{[1
]}

Córdova, A ^{[1
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 01期

关键词：

asymmetric catalysis; proline derivatives; alpha; beta-unsaturated aldehydes; epoxides;

D O I：

10.1016/j.tetlet.2005.10.128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organocatalytic asymmetric epoxidation of alpha, beta-unsaturated aldehydes with peroxides or sodium percarbonate is presented. Chiral pyrrolidine derivatives, proline and amino acid derived imidazolidinones mediate the asymmetric epoxidation of alpha,beta-unsaturated aldehydes. For example, commercially available protected alpha,alpha-diphenyl-2-prolinol catalyzes the asymmetric formation of 2-epoxy-aldehydes in 81-95% conversion with up to 96:4 dr and 98% ee. The use of non-toxic catalysts, aqueous solvents and hydrogen peroxide or sodium percarbonate as the oxygen sources makes the reaction environmentally benign. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：99 / 103

页数：5