Asymmetric induction in acyclic radical reactions: enantioselective syntheses of (s)-2-deuterioglycine and (r)-2-deuterioglycine.
1993
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.
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