Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles

Shuyou Chen, Delong Mu, Pei-Lin Mai, Jie Ke, Yingzi Li and Chuan He ()
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Shuyou Chen: Southern University of Science and Technology
Delong Mu: Southern University of Science and Technology
Pei-Lin Mai: Southern University of Science and Technology
Jie Ke: Southern University of Science and Technology
Yingzi Li: Southern University of Science and Technology
Chuan He: Southern University of Science and Technology

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract The exploitation of chirality at silicon in asymmetric catalysis is one of the most intriguing and challenging tasks in synthetic chemistry. In particular, construction of enantioenriched mediem-sized silicon-stereogenic heterocycles is highly attractive, given the increasing demand for the synthesis of novel functional-materials-oriented silicon-bridged compounds. Here, we report a rhodium-catalyzed enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles. This process undergoes a direct dehydrogenative C−H silylation, giving access to a wide range of triorgano-substituted silicon-stereogenic heterocycles in good to excellent yields and enantioselectivities, that significantly enlarge the chemical space of the silicon-centered chiral molecules. Further elaboration of the chiral monohydrosilane product delivers various corresponding tetraorgano-substituted silicon-stereogenic heterocycles without the loss of enantiopurity. These silicon-bridged heterocycles exhibit bright blue fluorescence, which would have potential application prospects in organic optoelectronic materials.

Date: 2021
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DOI: 10.1038/s41467-021-21489-6

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