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Synthesis 2002(15): 2296-2308
DOI: 10.1055/s-2002-34851
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Synthesis of anti-α-Hydroxy-β-Amino and anti-α,β-Diamino Acid Derivatives by Epoxidation of 1-Arylthio-1-nitroalkenes

Lydia Ambroise, Estelle Dumez, Andrea Szeki, Richard F. W. Jackson*
Department of Chemistry, Bedson Building, The University of Newcastle, Newcastle upon Tyne, NE1 7RU, UK
Fax: +44(114)2738673; e-Mail: r.f.w.jackson@shef.ac.uk;
Department of Chemistry, Dainton Building, Brook Hill, The University of Sheffield, Sheffield, S3 7HF, UK
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Publication History

Received 15 April 2002
Publication Date:
21 October 2002 (online)

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Abstract

Epoxidation of 1-tolylthio-1-nitroalkenes containing an allylic Boc-protected amino group yields cis-oxazolidinones 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-α,β-diamino acid derivatives.

Key words

amino acids - amino aldehydes - epoxides - epoxidation - stereoselective synthesis