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Stereodivergent Synthesis through Catalytic Asymmetric Reversed Hydroboration

Tao-Tao Gao, Wen-Wen Zhang, Xin Sun, Hou-Xiang Lu, Bi-Jie Li*

*Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing, 100084, China, Email: bijielimail.tsinghua.edu.cn

T.-T. Gao, W.-W. Zhang, X. Sun, H.-X. Lu, B.-J. Li, J. Am. Chem. Soc., 2019, 141, 4670-4677.

DOI: 10.1021/jacs.8b13520 (free Supporting Information)


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Abstract

A Rh-catalyzed hydroboration of α, β-unsaturated carbonyl compounds with pinacolborane proceeds with high levels of regio-, diastereo-, and enantioselectivities to provide products with two vicinal stereocenters. Through the appropriate choice of substrate geometry (E or Z) and ligand enantiomer, all possible diastereoisomers are readily accessible.

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Key Words

hydroxylation, sodium perborate


ID: J48-Y2019