Chemoenzymatic synthesis of β-hydroxyl-sulfoxides by a two-step reaction of enzymatic reduction using Pseudomonas monteilii species and sulfoxidation with chiral titanium complexe

A two-step enantioselective synthetic strategy for the preparation of β-hydroxyl-sulfoxides has been described. With the enzymatic reduction of β-ketosulfides using Pseudomonas monteilii ZMU-T04 followed by the asymmetric sulfoxidation with Ti(OiPr)4/(S)-BINOL complexe, a wide range of corresponding β-hydroxyl-sulfoxide derivatives were smoothly obtained with excellent stereoselectivities (up to 99:1 dr and >99% ee). A plausible chelate structure of titanium complexe in the asymmetric sulfoxidation of β-hydroxyl-sulfides was also proposed on the basis of control experiments.