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

Chen，Shuyou; Mu，Delong; Mai，Pei Lin; Ke，Jie; Li，Yingzi; He，Chuan

2021-12-01

10.1038/s41467-021-21489-6

Nature Communications   影响因子和分区

2041-1723

2041-1723

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.

SCI

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China[21901104] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Science & Technology - Other Topics

Multidisciplinary Sciences

WOS:000623781900023

NATURE RESEARCH

2-s2.0-85101360883

Scopus

Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,China

Chen，Shuyou,Mu，Delong,Mai，Pei Lin,et al. Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles[J]. Nature Communications,2021,12(1).

Chen，Shuyou,Mu，Delong,Mai，Pei Lin,Ke，Jie,Li，Yingzi,&He，Chuan.(2021).Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles.Nature Communications,12(1).

Chen，Shuyou,et al."Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles".Nature Communications 12.1(2021).