Stereodivergent Synthesis through Catalytic Asymmetric Reversed Hydroboration

Journal of the American Chemical Society
Tao-Tao GaoBi-Jie Li

Abstract

The control of chemo-, regio-, diastereo-, and enantioselectivity is a central theme in organic synthesis. The capability to obtain the full set of stereoisomers of a molecule would significantly enhance the efficiency for the synthesis of natural product analogues and creation of chiral compound libraries for drug discovery. Despite the tremendous progress achieved in the field of asymmetric synthesis in the past decades, the precise control of both relative and absolute configurations in catalyst-controlled reactions that create multiple stereocenters remains a significant synthetic challenge. We report here the development of a catalyst-controlled hydroboration with hitherto unattainable selectivity. The Rh-catalyzed hydroboration of α, β-unsaturated carbonyl compounds with pinacolborane proceeds with high levels of regio-, diastereo-, and enantioselectivities to provide a hydroboration product with two vicinal stereocenters. Through the appropriate choice of substrate geometry ( E or Z) and ligand enantiomer ( S or R), all the possible diastereoisomers are readily accessible. The boron-containing products underwent many stereospecific transformations, thus providing a strategy for collective stereodivergent synthesis of div...Continue Reading

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Citations

May 11, 2021·Journal of the American Chemical Society·Shao-Qian YangZhi-Tao He
Jul 14, 2021·Journal of the American Chemical Society·Wenke DongWanxiang Zhao
Sep 4, 2019·Journal of the American Chemical Society·Qinglong ZhangWeiwei Zi
Nov 21, 2019·Journal of the American Chemical Society·Xiao-Yan BaiBi-Jie Li
Mar 24, 2020·Organic Letters·Hongliang ZhaoSenmiao Xu
Dec 29, 2020·Journal of the American Chemical Society·Byungjun KimSarah Yunmi Lee
Oct 6, 2021·Chemical Communications : Chem Comm·Byungjun KimSarah Yunmi Lee
Oct 29, 2021·Chemical Society Reviews·Jiefeng HuTodd B Marder
Jan 7, 2022·Journal of the American Chemical Society·Daniel RozsarDarren J Dixon
Dec 15, 2021·Angewandte Chemie·Enrico BergamaschiChristopher J Teskey

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