Novel syntheses of chiral beta- and gamma-amino acid derivatives utilizing N-protected (aminoacyl)benzotriazoles from aspartic and glutamic acids

J Org Chem. 2007 Jan 19;72(2):407-14. doi: 10.1021/jo061667s.

Abstract

Friedel-Crafts reactions of N-protected (alpha-aminoacyl)benzotriazoles with hetero- and benzenoid- aromatics give alpha-amino ketones that can be reduced by either triethyl silane or sodium borohydride to form the corresponding beta- and gamma-amino acid derivatives. The preservation of chirality throughout this process is confirmed by chiral HPLC results.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Aspartic Acid / chemistry*
  • Glutamic Acid / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Triazoles / chemistry*

Substances

  • Amino Acids
  • Triazoles
  • Aspartic Acid
  • Glutamic Acid
  • benzotriazole