Asymmetric Induction in Acyclic Radical Reactions: Enantioselective Syntheses of (S)-2-Deuterioglycine and (R)-2-Deuterioglycine.

Abstract The (-)-8-phenylmenthol esters of N-Boc-glycine and N-Boc-2,2-dideuterioglycine were brominated with N-bromosuccinimide and the bromo compounds were reduced with tri-n-butyldeuteriostannane and tri-n-butylstannane respectively, to give the chiral glycine derivatives in 90% optical yield. Hydrolysis yielded the amino acid without racemisation.