Catalytic Enantioconvergent Conjugate Addition of Organosilanes via a Strategy of Fluorodesilylation

Abstract

Fluorodesilylation is a widely used strategy to activate organosilanes as nucleophiles for the development of organic transformations. To date, highly enantioselective catalytic fluorodesilylations have been limited to the activation of silyl ethers, organosilanes bearing specific substituents such as trifluoromethyl and cyanide, allylsilanes, and acylsilanes. However, the catalytic enantioconvergent reaction of racemic organosilanes bearing variable substituents via fluorodesilylation has been rarely reported. We report an unprecedented enantioconvergent fluorodesilylation of racemic organosilanes bearing various substituents with a chiral ammonium fluoride. Notably, these results demonstrated that the fluorodesilylation could potentially be a general strategy for the development of catalytic asymmetric reactions of racemic organosilanes.