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Stereocontrolled synthesis of anti-alpha-hydroxy-beta-amino and anti-alpha,beta-diamino acid derivatives by epoxidation of 1-arylthio-l-nitroalkenes

Lookup NU author(s): Dr Estelle Dumez, Professor Richard Jackson

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Abstract

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.

Publication metadata

Author(s): Ambroise L, Dumez E, Szeki A, Jackson RFW

Publication type: Article

Publication status: Published

Journal: Synthesis

Year: 2002

Issue: 15

Pages: 2296-2308

ISSN (print): 0039-7881

ISSN (electronic): 1437-210X

Publisher: Georg Thieme Verlag

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