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...

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Bibliographic Details
Published in:Tetrahedron 2017-08, Vol.73 (34), p.5200-5206
Main Authors: Cui, Baodong, Yang, Min, Shan, Jing, Qin, Lei, Liu, Ziyan, Wan, Nanwei, Han, Wenyong, Chen, Yongzheng
Format: Article
Language:English
Subjects:
Biocatalysis
Sulfoxidation
Titanium complexe
Two-step reaction
β-Hydroxyl-sulfoxides
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.07.014