Recyclable and Stable α-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free C,N-Unprotected α-Amino Acids

Molecules. 2019 Jun 13;24(12):2218. doi: 10.3390/molecules24122218.

Abstract

A novel special designed, stable, and recyclable chiral ligand bearing a quaternary carbon was developed for chemical dynamic kinetic resolution (DKR) of free C,N-unprotected racemic α-amino acids via Schiff base intermediates. This method furnishes high yields with excellent enantioselectivity, has a broad substrate scope, and uses operationally simple and convenient conditions. The present chemical DKR is a practical and useful method for the preparation of enantiopure α-amino acids.

Keywords: Schiff base intermediates; dynamic kinetic resolution; ligands; quaternary carbon; unprotected α-amino acids.

MeSH terms

  • Amino Acids / chemistry*
  • Carbon / chemistry
  • Kinetics
  • Proline / analogs & derivatives*
  • Proline / chemistry
  • Schiff Bases / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Schiff Bases
  • 2-methylproline
  • Carbon
  • Proline