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

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. Enantioenriched medium-sized silicon-stereogenic heterocycles are in high demand due to the potential use in functional materials. Here, the authors show a rhodium-catalyzed enantioselective synthesis of six- and seven-membered tri-organosubstituted silicon-stereogenic heterocycles.

Automated summary

The authors present a rhodium-catalyzed enantioselective synthesis of six- and seven-membered tri-organosubstituted silicon-stereogenic heterocycles, which significantly expand the chemical space of silicon-centered chiral molecules and show potential application prospects in the field of organic optoelectronic materials.