CONTROL OF DIASTEREOFACIAL SELECTIVITY IN THE NUCLEOPHILIC EPOXIDATION OF GAMMA-OXYGENATED-ALPHA,BETA-UNSATURATED SULFONES

被引：23
|
作者：
JACKSON, RFW
STANDEN, SP
CLEGG, W
机构：
[1] Department of Chemistry, Bedson, Building, The University, Newcastle upon Tyne
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 39期
关键词：
MICHAEL ADDITION; VINYLSULPHONE; EPOXIDATION; ALLYLIC STEREOCHEMISTRY;
D O I：
10.1016/S0040-4039(00)92395-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Epoxidation of gamma-oxygenated-alpha,beta-unsaturated sulphones 4-8 with lithium t-butyl hydroperoxide proceeds with moderate to high diastereoselectivity to give 2-phenylsulphonyl oxiranes 9-13. The sense of diastereoselectivity is dependent on the steric bulk of the alkyl substituent at the gamma-centre.
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页码：5393 / 5396
页数：4
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