Copper-catalyzed enantioselective sulfonylation from sulfur dioxide: generation of tertiary propargylic sulfones†

Abstract

Enantioselective sulfonylation through a copper-catalyzed three-component reaction of propargylic cyclic carbonates, cyclopropan-1-ols and sulfur dioxide is reported, allowing the preparation of tertiary propargylic sulfones with quaternary stereocenters. This enantioselective propargylic sulfonylation proceeds under mild conditions through γ-keto sulfinate intermediates and copper–allenylidene intermediates, featuring high asymmetric induction and wide functional group compatibility.