The ability to diastero- and enantioselectively install vicinal functional groups on alkenes constitutes one of the workhorse methods of asymmetric organic synthesis. However, for the most part these methods are limited to the introduction of oxygen and nitrogen-based functional groups and in recent years also halogens. Remarkably, the introduction of sulfur containing groups together with other heteroatoms with this level of stereocontrol has lagged behind. The concept of "Lewis base activation of Lewis acids" developed in these laboratories over the past 15 years provides a unique paradigm for the activation of Main Group elements. This lecture will describe the evolution of highly general and selective sulfenofunctionalization reactions of isolated double bonds from both a preparative and mechanistic perspective.

Catalytic, enantioselective synthesis of sulfur-containing compounds: An homage to Eric Block

251st National Meeting (2016)

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