VERSATILE SYNTHON FOR CHIRALLY BETA-DEUTERATED L-AMINO-ACIDS AND SYNTHESIS OF (3R)-[3-H-2(1)]-L-SERINE AND (3S)-[3-H-2(1)]-L-SERINE

A divergent and highly enantioselective synthetic methodology for prod ucing chirally beta-deuterated L-amino acids was developed. This metho d is based upon the chirality transcription approach, using diacetone- D-glucos-3-ulose (1) as a template. (N-benzyl)methylthioformimidoyl-D- allo-derivatives (3b and 3c), which are easily accessible from 1, were subjected to halonium ion-assisted cyclization to afford highly diast ereoselectively and efficiently versatile 5-membered cyclic carbamate synthons having a stereochemically defined deuterated halomethyl group (4c and 4d, respectively). Subsequent straightforward transformation of these synthons gave rise to (3R)- and (3S)-[3-H-2(1)]-L-serine. Fur ther transformation of the crucial halomethyl group of 4a-c was also p ursued to extend this methodology.