The origin of the stereoselectivity in the asymmetric Michael reaction using chiral imines secondary enamines under neutral conditions: a computational investigation

被引：22

作者：

Dau, METH

Riche, C

Dumas, F

d'Angelo, J

机构：

[1] CNRS, Inst Chim Subst Nat, F-91128 Gif Sur Yvette, France

[2] Univ Paris Sud, Ctr Etud Pharmaceut, CNRS, Unite Chim Organ, F-92296 Chatenay Malabry, France

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(98)00063-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The diastereoselectivity in the asymmetric Michael reaction using chiral imines/secondary enamines under neutral conditions has been investigated with the help of AM1 calculations. The energetic differences between the two competing transition states involving enamino ketones 7d, 7g and methyl acrylate are in good agreement with the stereoselectivities observed with the corresponding chiral imines, derived from 1-phenylethylamine (de 95%) and from 1-cyclohexylethylamine (de 45%). The calculated transition structures indicate that steric factors govern the pi-facial discrimination. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1059 / 1064

页数：6

共 15 条

[1] THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES UNDER NEUTRAL CONDITIONS - STEREOCHEMICAL EVIDENCES IN SUPPORT OF A CYCLIC TRANSITION-STATE [J].