Research in the M. P. Watson Group is centered on the discovery of new catalytic, stereoselective methods for organic synthesis by utilizing the power of both transition metal and Brønsted acid catalysts. These methods will allow greater efficiency and novel bond constructions in the synthesis of stereochemically complex molecules, with applications that extend to natural products synthesis, drug discovery and process chemistry. The development of these methods will also provide a platform for mechanistic investigations, which will provide insights into questions of fundamental reactivity and catalyst design.
Selective Activation of Relatively Strong Bonds
One project within our group is focused on the selective activation of relatively strong bonds by transition metal catalysts. Extremely powerful methods, such as the Heck, Suzuki and Buchwald-Hartwig reactions, have been enabled by the observation that transition metal catalysts selectively activate weak carbon–halide and carbon–oxygen bonds. The development of catalysts for the selective activation of relatively strong C–X bonds and incorporation of both the C- and X-fragments into the products would allow an efficient bond disconnection approach for the formation of highly substituted olefin or alkane products from simple starting materials. The application of homochiral metal catalysts for enantioselective variants of these transformations is also being investigated.
Brønsted Acid-Catalyzed Reactions of Unactivated Olefins
Another project is directed toward the design of new chiral Brønsted acid catalysts for additions across unactivated olefins. We are working to synthesize chiral Brønsted acid catalysts that are more acidic than currently available chiral Brønsted acids and are capable of participating in secondary stabilizing interactions with the substrate. These Brønsted acids have the potential to catalyze highly enantioselective additions of H–X (X = C, O, N, etc.) across olefins, allowing rapid access to a variety of biologically active molecules.
