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Lookup NU author(s): Dr Estelle Dumez,
Professor Richard Jackson
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Epoxidation of 1-tolylthio-1-nitroalkenes containing an allylic Boc-protected amino group yields cis-oxazolidmones 13, formed by intramolecular trapping of the presumed intermediate epoxides by the carbamate group. Epoxidation of the analogous Z- or Fmoc-protected derivatives yields the corresponding syn-epoxides which, although they cannot be isolated, can be trapped with aqueous ammonia, or more efficiently benzylamine, to give stereoisomerically pure anti-alpha,beta-diamino acid derivatives.
Author(s): Ambroise L, Dumez E, Szeki A, Jackson RFW
Publication type: Article
Publication status: Published
ISSN (print): 0039-7881
ISSN (electronic): 1437-210X
Publisher: Georg Thieme Verlag