Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles.
Nat Commun
; 12(1): 1249, 2021 02 23.
Article
em En
| MEDLINE
| ID: mdl-33623025
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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Nat Commun
Ano de publicação:
2021
Tipo de documento:
Article