Oxazolinyloxiranyllithium-mediated stereoselective synthesis of alpha-epoxy-beta-amino acids

Org Lett. 2003 Jul 24;5(15):2723-6. doi: 10.1021/ol034927q.

Abstract

[reaction: see text] The stereoselective synthesis of novel alpha-epoxy-beta-amino acids is described by a route that combines the chemistry of oxazolinyloxiranyllithiums with that of nitrones. The intermediate trioxadiazadispiro[2.0.4.3]undecanes 4 have been isolated and converted by hydrolysis into epoxy-5-isoxazolidinones 5 which can be transformed into the alpha-epoxy-beta-amino acids 8 by N-O reduction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Epoxy Compounds / chemical synthesis*
  • Lithium / chemistry*
  • Nitrogen Oxides / chemistry
  • Organometallic Compounds / chemistry*
  • Oxazolidinones / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Amino Acids
  • Epoxy Compounds
  • Nitrogen Oxides
  • Organometallic Compounds
  • Oxazolidinones
  • Lithium