DIASTEREOSELECTIVITY IN THE MICHAEL-TYPE ADDITION OF IMINES REACTING AS THEIR SECONDARY ENAMINE TAUTOMERS

被引：30

作者：

PFAU, M ^{[1
]}

TOMAS, A ^{[1
]}

LIM, S ^{[1
]}

REVIAL, G ^{[1
]}

机构：

[1] UNIV PARIS 05,PHYS LAB,F-75270 PARIS 06,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 05期

关键词：

D O I：

10.1021/jo00110a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael-type reactions of 2-methyl(benzylimino)cyclohexane (reacting as its secondary enamine tautomer 1) were performed with methyl methacrylate (2), methyl crotonate (5), and maleic anhydride (7). In each case, the stereochemical relationship of the substituents in the major cyclized adducts 4, 6, and 8 obtained with excellent diastereoselectivities was shown to be the one predicted in a previous theoretical calculation which established that the complex of the reactants has a chairlike geometry. The predicted concomitant H-transfer and C-C bond formation in these reactions was also confirmed in the methyl methacrylate case. Besides, these experiments have shown that regioisomers are formed in appreciable amounts when substituted electrophilic olefins are used.

引用

页码：1143 / 1147

页数：5

共 19 条

[1] THE ASYMMETRIC MICHAEL ADDITION PROCESS INVOLVING CHIRAL IMINES - STEREOCHEMICAL DATA IN SUPPORT OF A CYCLIC-LIKE TRANSITION-STATE [J].