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

Article abstract of DOI:10.1016/S0040-4020(01)80156-3

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.