ENANTIOSELECTIVE SYNTHESIS OF (S)-VIGABATRIN(R)

An asymmetric synthesis of fully protected (S)-Vigabatrin(R) has been developed. The key intermediate in the sequence is enantiomerically pu re N-Boc-5-phenyl-3-amino-1,2-diol 5a, obtained from (E)-5-phenyl-2-pe nten-1-ol by employing a catalytic Sharpless epoxidation as the sole s ource of chirality. Aminodiol 50 was converted into the target N-Boc-( S)-Vigabatrin methyl ester 3 by a five-step sequence involving the act ualization of the latent carboxyl group (phenyl oxidation) and a Corey -Hopkins deoxygenative protocol of the 1,2-diol. (C) 1997 Elsevier Sci ence Ltd.