Asymmetric induction in radical reactions: enantioselective syntheses of (S)-2-deuterioglycine and (R)-2-deuterioglycine

Abstract

The (–)-8-phenylmenthol ester of N-Boc-glycine is brominated with N-bromosuccinimide and the bromo-compound is reduced with tri-n-butyldeuteriostannane to give the chiral glycine derivative in high optical yield which upon hydrolysis yields the amino acid without racemisation.