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Synthesis 2002(15): 2296-2308
DOI: 10.1055/s-2002-34851
DOI: 10.1055/s-2002-34851
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New YorkStereocontrolled Synthesis of anti-α-Hydroxy-β-Amino and anti-α,β-Diamino Acid Derivatives by Epoxidation of 1-Arylthio-1-nitroalkenes
Weitere Informationen
Received
15 April 2002
Publikationsdatum:
21. Oktober 2002 (online)
Publikationsverlauf
Publikationsdatum:
21. Oktober 2002 (online)
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
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