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Synlett 2001; 2001(8): 1214-1216
DOI: 10.1055/s-2001-16047
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Stereoselective Synthesis of Differentially Protected anti-α,β-Diamino Acid Derivatives using Arylthionitrooxiranes

Estelle Dumez* , Andrea Szeki, Richard F. W. Jackson
  • *Department of Chemistry, Bedson Building, The University of Newcastle upon Tyne, Newcastle upon Tyne, NE1 7RU, UK
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Publication Date:
31 December 2001 (online)

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Epoxidation of 1-tolylthio-1-nitroalkenes containing an allylic Z- or Fmoc-protected amino group yields the corresponding syn-epoxides which, although they cannot be isolated, can be trapped with aqueous ammonia to give stereoisomerically pure anti-α,β-diamino acid derivatives.

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