Stereoselective synthesis of novel 4,5-epoxy-1,2-oxazin-6-ones and alpha,beta-epoxy-gamma-amino acids from beta-lithiated oxazolinyloxiranes and nitrones

Org Lett. 2006 Oct 12;8(21):4803-6. doi: 10.1021/ol0618609.

Abstract

[reaction: see text] A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5]decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-gamma-amino acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Lithium / chemistry*
  • Nitrogen Oxides / chemistry*
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry
  • Oxazoles / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Epoxy Compounds
  • Nitrogen Oxides
  • Oxazines
  • Oxazoles
  • nitrones
  • Lithium