Toggle Main Menu Toggle Search

Open Access padlockePrints

The Newcastle University research output collection, currently available on ePrints, will shortly be moving to a new open repository platform, Figshare. To prepare for the data migration we have paused adding new content to ePrints, and will resume once the new repository is launched. During this time you will continue to have access to ePrints (but no new content will appear). We will share updates here when available.

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

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.

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

Share