Efficient synthesis of beta2-amino acid by homologation of alpha-amino acids involving the Reformatsky reaction and Mannich-type imminium electrophile

J Org Chem. 2006 Apr 14;71(8):3332-4. doi: 10.1021/jo060316a.

Abstract

Development of new methods for the synthesis of beta-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of beta2-amino acids by homologation of alpha-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.

MeSH terms

  • Amination
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Bromine / chemistry
  • Electrons*
  • Esters / chemical synthesis
  • Esters / chemistry
  • Fluoroacetates / chemistry
  • Mannich Bases / chemistry
  • Methylation
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Esters
  • Fluoroacetates
  • Mannich Bases
  • Quaternary Ammonium Compounds
  • fluoroacetic acid
  • Bromine