Stereoselective synthesis of 2(S)-(1,1-dimethylethylsulfonylmethyl)-3-(1- naphthyl)-propionic acid, building block for protease inhibitors via asymmetric hydrogenation

Article abstract of DOI:10.1016/S0040-4020(01)85008-0

Title compound 1b (purity > 99%, 99.6% ee) is synthesized (100g scale) from commercial 3-bromo-pyruvic acid in six steps with an overall yield of 16%. The sequence is operationally simple and devoid of chromatographic purifications. Key step is the asymmetric hydrogenation of a substrate with sulfur functionality.