Chemical approach for interconversion of (S)- and (R)-α-amino acids

Org Biomol Chem. 2013 Jul 21;11(27):4503-7. doi: 10.1039/c3ob40541a.

Abstract

Here we report a general method for the preparation of unnatural (R)-α-amino acids via complexation of α-(phenyl)ethylamine derived chiral reagent (S)- with various (S)-α-amino acids. The reactions proceed with synthetically useful chemical yields and thermodynamically controlled diastereoselectivity. Chiral reagent (S)- can be conveniently recovered and reused without any loss of enantiomeric purity and reactivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Indicators and Reagents
  • Phenethylamines / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • Indicators and Reagents
  • Phenethylamines