Synthesis of cyclic and acyclic beta-amino acids via chelation-controlled 1,3-dipolar cycloaddition

J Org Chem. 2003 Oct 31;68(22):8739-41. doi: 10.1021/jo034940o.

Abstract

Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic beta-amino acid derivatives.

MeSH terms

  • Acids, Acyclic / chemical synthesis*
  • Amines / chemistry
  • Amino Acids / chemical synthesis*
  • Catalysis
  • Chelating Agents / chemistry
  • Cyclization
  • Glycine / analogs & derivatives*
  • Glycine / chemistry
  • Isoxazoles / chemistry
  • Nitrogen Oxides / chemistry
  • Stereoisomerism

Substances

  • Acids, Acyclic
  • Amines
  • Amino Acids
  • Chelating Agents
  • Isoxazoles
  • Nitrogen Oxides
  • nitrones
  • N-phenylglycine
  • Glycine