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

被引：156
|
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
收藏
页码：1464 / 1467
页数：4
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