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

Authors
JACKSON RFW KIRK JM PALMER NJ WATERSON D WYTHES MJ
Citation
Rfw. Jackson et al., CONTROL OF DIASTEREOSELECTIVITY IN THE NUCLEOPHILIC EPOXIDATION OF 1-ARYLTHIO-1-NITROALKENES - SYNTHESIS OF DIASTEREOISOMERICALLY PURE GAMMA-HYDROXY THREONINE DERIVATIVES, Journal of the Chemical Society, Chemical Communications, (11), 1993, pp. 889-891
Citations number
14
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
11
Year of publication
1993
Pages
889 - 891
Database
ISI
SICI code
0022-4936(1993):11<889:CODITN>2.0.ZU;2-2
Abstract
Epoxidation of the 1-nitro-1-(p-tolylthio)alkene 1 derived from D-isop ropylideneglyceraldehyde with lithium tert-butyl peroxide affords the syn epoxide 2 with moderate selectivity, whereas epoxidation with pota ssium tert-butyl peroxide affords the anti diastereoisomer 3 preferent ially; treatment of each of the epoxides 2 and 3 with amines, includin g ammonia, gives diastereoisomerically pure alpha-amino thioesters wit h no trace of stereoisomeric contamination.