Streamlined Construction of Silicon-Stereogenic Silanes by Tandem Enantioselective C-H Silylation/Alkene Hydrosilylation

Journal of the American Chemical Society
Delong MuChuan He

Abstract

A rhodium-catalyzed tandem enantioselective C-H silylation/alkene hydrosilylation of dihydrosilanes, which enables the streamlined construction of a wide range of silicon-stereogenic silanes, is successfully developed. This process involves a SiH2-steered highly enantioselective C-H silylation to furnish the corresponding desymmetric monohydrosilanes, which are subsequently trapped with alkenes in a stereospecific fashion to build functionally diverse asymmetrically tetrasubstituted silanes. This general strategy combines readily available dihydrosilanes and alkenes to construct various enantioenriched silicon-stereogenic silanes, including 9-silafluorenes, Si-bridged ladder compounds, and benzosilolometallocenes, in a single step with good to excellent yields and enantioselectivities.

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Citations

Feb 3, 2021·Journal of the American Chemical Society·Shao-Jie LouZhaomin Hou
Feb 5, 2021·Angewandte Chemie·Jie KeChuan He
Mar 19, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Gilles LemièreLouis Fensterbank
Sep 28, 2021·Journal of the American Chemical Society·Bing ZuChuan He

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