Diastereoselectivity in the epoxidation of substituted cyclohexenes by dimethyldioxirane

被引：87
|
作者：
Murray, RW
Singh, M
Williams, BL
Moncrieff, HM
机构：
[1] Department of Chemistry, University of Missouri - St. Louis, St. Louis
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 05期
关键词：
D O I：
10.1021/jo951864j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three series of compounds based on the cyclohexene framework. have been epoxidized by dimethyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole-dipole influences on the epoxide stereochemistry.
引用
收藏
页码：1830 / 1841
页数：12
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