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. 2021 Jun 14;60(25):13887-13891.
doi: 10.1002/anie.202103748. Epub 2021 May 17.

Catalytic Asymmetric Synthesis of Silicon-Stereogenic Dihydrodibenzosilines: Silicon Central-to-Axial Chirality Relay

Yonghong Guo  1 , Meng-Meng Liu  1 , Xujiang Zhu  1 , Liru Zhu  1 , Chuan He  1
Affiliations

Catalytic Asymmetric Synthesis of Silicon-Stereogenic Dihydrodibenzosilines: Silicon Central-to-Axial Chirality Relay

Yonghong Guo et al. Angew Chem Int Ed Engl. .

Abstract

A Rh-catalyzed asymmetric synthesis of silicon-stereogenic dihydrodibenzosilines featuring axially chiral 6-membered bridged biaryls is demonstrated. In the presence of a RhI catalyst with a chiral diphosphine ligand, a wide range of dihydrodibenzosilines containing both silicon-central and axial chiralities are conveniently constructed in excellent enantioselectivities via dehydrogenative C(sp3 )-H silylation. Absolute configuration analysis by single-crystal X-ray structures revealed a novel silicon central-to-axial chirality relay phenomenon, which we believe will inspire further research in the field of asymmetric catalysis and chiroptical materials.

Keywords: axial chirality; chirality relay; enantioselective C−H silylation; silicon-central chirality; silicon-stereogenic monohydrosilanes.

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