Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-Containing Dipeptides: Improved Stereoinduction under Solvent-Free Conditions

被引：159

作者：

Hernandez, Jose G. ^{[1
]}

Juaristi, Eusebio ^{[1
]}

机构：

[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 05期

关键词：

SMALL PEPTIDES; CATALYSTS; EFFICIENT; WATER;

D O I：

10.1021/jo1022469

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organocatalytic activity of the methyl ester of (S)-proline-(S)-phenylalanine, (S,S)-2, in the asymmetric aldol reaction between cyclohexanone and acetone with various aromatic aldehydes under solvent-free conditions in a ball mill has been evaluated. alpha,alpha-Dipeptide (S,S)-2 catalyzed the stereoselective formation of the expected aldol products, with higher diastereo- and enantioselectivity relative to similar reactions in solution, up to 91:9 anti:syn diastereomeric ratio and up to 95% enantiomeric excess.

引用

页码：1464 / 1467

页数：4