Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes
Kailin Yin, Jinyu Zhang, Deng Pan, Shuhan Chen, Chen Song, Yufeng Shi, Genping Huang, Dongbing Zhao
Abstract
The diverse utility of acyclic vinylsilanes has driven the interest in the synthesis of enantioenriched vinylsilanes bearing a Si-stereogenic center. However, the predominant approaches for catalytic asymmetric generation of Si-stereogenic vinylsilanes have mainly relied on transition metal-catalyzed reactions of alkynes with different silicon sources. Here we successfully realize the enantioselective synthesis of linear silicon-stereogenic vinylsilanes with good yields and enantiomeric ratios from simple alkenes under rhodium catalysis. The significance of this transformation lies in its ability to achieve regioconvergent and enantioconvergent conversion, efficiently transforming petroleum-derived isomeric mixtures of olefin feedstocks into a single regio- and stereoisomer product. The practicality of this method is further exemplified by the diverse downstream transformations of these enantioenriched silicon-stereogenic vinylsilanes leveraging the olefin functionality and the leaving group nature of the aryl substituent on silicon as well as the development of chiral π-conjugated double bond systems. The enantioselective synthesis of silicon-stereogenic vinylsilanes from simple alkenes remains underexplored. Here the authors report the enantioselective method from simple alkenes to yield linear silicon-stereogenic vinylsilanes with good yields and enantiomeric ratios under rhodium catalysis.