Tetrahedron
Tetrahedron
5 years ago

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

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(O i Pr)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.

Publisher URL: www.sciencedirect.com/science

DOI: S004040201730738X

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