Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 25, Pages 13887-13891Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202103748
Keywords
axial chirality; chirality relay; enantioselective C− H silylation; silicon-central chirality; silicon-stereogenic monohydrosilanes
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Funding
- National Natural Science Foundation of China [21901104]
- Southern University of Science and Technology, Shenzhen Science and Technology Innovation Committee [JCYJ20190809142809370]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
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A Rh-catalyzed asymmetric synthesis of silicon-stereogenic dihydrodibenzosilines featuring axially chiral 6-membered bridged biaryls is demonstrated in the study. Various dihydrodibenzosilines containing both silicon-central and axial chiralities are conveniently constructed in excellent enantioselectivities via dehydrogenative C(sp(3))-H silylation with a Rh-I catalyst with a chiral diphosphine ligand. The analysis of absolute configuration by single-crystal X-ray structures reveals a novel silicon central-to-axial chirality relay phenomenon, which is believed to inspire further research in asymmetric catalysis and chiroptical materials.
A Rh-catalyzed asymmetric synthesis of silicon-stereogenic dihydrodibenzosilines featuring axially chiral 6-membered bridged biaryls is demonstrated. In the presence of a Rh-I 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(sp(3))-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.
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