Enantioselective Geminal Olefin Disulfonoxylation

Here, we report the first examples of enantioselective geminal olefin disulfonoxylation reactions. Our reaction protocol is operationally simple and involves stirring the olefin substrate with an enantiopure hypervalent iodine reagent in the presence of 2 equiv of a sulfonic acid in dichloromethane. No special precautions to exclude air or ambient moisture are necessary. We have conducted a thorough investigation of the substrate scope with respect to both the olefin substrate and the sulfonic acid partner. The reaction scales well, and the scalemic products serve as versatile chirons.