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Molybdenum-Catalyzed Diastereoselective anti-Dihydroxylation of Secondary Allylic Alcohols

Shixia Su, Chuan Wang*

*Department of Chemistry, Center for Excellence in Molecular Synthesis, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China, Email: chuanwustc.edu.cn

S. Su, C. Wang, Org. Lett., 2019, 21, 2436-2440.

DOI: 10.1021/acs.orglett.9b00735 (free Supporting Information)


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Abstract

A Mo-catalyzed anti-dihydroxylation of secondary allylic alcohols provides 1,2,3-triols bearing up to three continuous stereocenters with excellent diastereocontrol. The excellent diastereomeric ratios of the final triol products can be achieved due to the high level of both diastereocontrol in the initial epoxidation and regiocontrol in the following hydrolysis in situ.

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Key Words

dihydroxylation, hydrogen peroxide


ID: J54-Y2019