Synthesis of alpha-amino acid precursors directly from aldehydes using masked acyl cyanide reagents and N,O-dialkylated hydroxylamines

J Org Chem. 2006 Aug 4;71(16):6038-43. doi: 10.1021/jo0607515.

Abstract

A synthetic methodology for the synthesis of alpha-amino acid precursors directly from the corresponding aldehydes using N,O-dialkylated hydroxylamines and masked acyl cyanide (MAC) reagents was developed. The one-pot reaction can be carried out under mild conditions and without a separate purification step of the imino species. The method was applied to the synthesis of optically pure (+)-4-methylphenylglycine and the derivatives by using an Abiko-Masamune's tricyclic 1,2-oxazolidine as the chiral auxiliary.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry
  • Aldehydes / chemistry*
  • Alkylation
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry*
  • Cyanides / chemistry*
  • Hydroxylamine / chemistry*
  • Molecular Structure
  • Nitrogen / chemistry*
  • Oxygen / chemistry*
  • Temperature

Substances

  • Acetonitriles
  • Aldehydes
  • Amino Acids
  • Cyanides
  • Hydroxylamine
  • Nitrogen
  • Oxygen
  • acetonitrile