Improvement of the asymmetric induction from lactic acid derivatives enhanced by ZnCl2

被引：0
|
作者：
Huettenhain, Stefan H. [1 ]
机构：
[1] Fachbereich Chem & Biotechnol, Hochschule Darmstadt, D-64289 Darmstadt, Germany
来源：
SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 7-9期
关键词：
ketone hydroboration; lactic acid derivatives; solvent-induced chirality;
D O I：
10.1080/00397910701198930
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lactic acid methyl ester, lactic acid ethyl ester, and (2S)-ethyl-2-methoxy propanate were used as solvents for acetophenone reduction by boron hydrides. Moderate enantiomeric excess up to 60% was obtained in the presence of stoichiometric amounts of ZnCl2. There is evidence for an intermediate between the solvents, the Lewis acid and the ketone, as the prerequisite for chirality transfer. The importance of the Lewis acid is to strengthen interaction between solvent and educt compared to the hydroxy group.
引用
收藏
页码：1141 / 1146
页数：6
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