Proline-catalyzed, asymmetric mannich reactions in the synthesis of a DPP-IV inhibitor

J Org Chem. 2006 Jan 6;71(1):390-2. doi: 10.1021/jo0519458.

Abstract

[reaction: see text] A highly stereoselective L-proline-catalyzed, asymmetric direct Mannich reaction between a glyoxalate-derived imine and phenyl acetaldehyde was employed for the formation of a syn substituted beta-phenyl homoserine. This Mannich adduct was then readily elaborated to a functionalized beta-phenyl aspartic acid derivative through a series of mild and efficient transformations.

MeSH terms

  • Aldehydes / chemistry
  • Amino Alcohols / chemistry
  • Catalysis
  • Dipeptidyl Peptidase 4 / metabolism*
  • Molecular Structure
  • Proline / chemistry*
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology
  • Stereoisomerism

Substances

  • Aldehydes
  • Amino Alcohols
  • Protease Inhibitors
  • Proline
  • Dipeptidyl Peptidase 4