A protocol for an asymmetric synthesis of γ-amino acids

J Org Chem. 2012 Jul 20;77(14):6296-301. doi: 10.1021/jo301177f. Epub 2012 Jul 6.

Abstract

A new and practical method for the asymmetric synthesis of γ-amino acids from β,γ-butenolides by an in situ esterification, condensation, and reduction in a one-pot procedure is described. This method is quite general for the preparation of both enantiomers of aryl or aliphatic γ-amino acids in high yields. These γ-amino-acid derivatives were also shown to be versatile synthetic intermediates for further transformations by their conversion to γ-lactams, δ-amino alcohols, and hydrolysis products in high yields with no racemization.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemistry
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amino Acids
  • butenolide
  • 4-Butyrolactone