Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids

Org Biomol Chem. 2014 Aug 28;12(32):6239-49. doi: 10.1039/c4ob00669k. Epub 2014 Jul 10.

Abstract

This work presents the first chemical approach for the resolution of α-amino acids offering the following advantages: (1) The specially designed resolving reagent is derived from α-(phenyl)ethylamine, the most inexpensive chiral auxiliary, which can be recycled and reused, rendering the cost structure of the complete process very attractive; (2) the time-efficient two-step process can be conducted under operationally convenient conditions with virtually quantitative yields; and (3) the process can readily be adapted to large-scale use.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Chromatography, High Pressure Liquid
  • Crystallography, X-Ray
  • Glycine / chemistry
  • Ligands
  • Phenethylamines / chemical synthesis*
  • Phenethylamines / chemistry*
  • Schiff Bases / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • Ligands
  • Phenethylamines
  • Schiff Bases
  • Glycine