Sulfur dioxide (SO2), as an atmospheric pollutant, has been increasingly attracting the interest of scientists regarding its chemical utilization. Vicinal sulfonyl-functionalization of alkenes through SO2 insertion offers an innovative method to introduce both sulfonyl and other functional groups into a single molecule. This approach boosts compound diversity while eliminating the need for multi-step operations. On the other hand, asymmetric construction of quaternary all-carbon stereocenters remains a persistent synthetic challenge. In particular, methods for the synthesis of chiral sulfones bearing an all-carbon quaternary stereocenter are rare. Herein, we present a copper-catalyzed vicinal cyano-arylsulfonylation of acrylamides via the insertion of sulfur dioxide (SO2), providing an easy access to achieve this goal with minimally functionalized starting materials. The reaction proceeds under mild conditions through a verified single-electron-transfer (SET) mechanism with excellent enantioselectivity (mostly >99% ee), good functional group tolerance, and a broad substrate scope (>50 examples). Notably, this four-component reaction is applicable to the direct chiral functionalization of amino acid and peptide derivatives.

You have access to this article

Please wait while we load your content... Something went wrong. Try again?