CONTROL OF DIASTEREOSELECTIVITY IN THE NUCLEOPHILIC EPOXIDATION OF 1-ARYLTHIO-1-NITROALKENES - SYNTHESIS OF DIASTEREOISOMERICALLY PURE GAMMA-HYDROXY THREONINE DERIVATIVES

被引：17

作者：

JACKSON, RFW

KIRK, JM

PALMER, NJ

WATERSON, D

WYTHES, MJ

机构：

[1] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

[2] PFIZER LTD,SANDWICH CT13 9NJ,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 11期

关键词：

D O I：

10.1039/c39930000889

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Epoxidation of the 1-nitro-1-(p-tolylthio)alkene 1 derived from D-isopropylideneglyceraldehyde with lithium tert-butyl peroxide affords the syn epoxide 2 with moderate selectivity, whereas epoxidation with potassium tert-butyl peroxide affords the anti diastereoisomer 3 preferentially; treatment of each of the epoxides 2 and 3 with amines, including ammonia, gives diastereoisomerically pure alpha-amino thioesters with no trace of stereoisomeric contamination.

引用

页码：889 / 891

页数：3

共 14 条

[1] PREPARATION OF ALPHA-SUBSTITUTED S-PHENYLTHIO ESTERS FROM 2-NITRO-2-PHENYLTHIO OXIRANES [J].