Research Interests

We are an organometallic lab focused on the development of new synthetic methodologies to address difficulties in target-oriented synthesis. To control specificity, nature has evolved enzymes that perform chemical reactions with exquisite chemo-, diastereo-, and enantioselectivity.  Our main goal is to develop new small molecule transition metal catalysts that exhibit synthetically useful levels of selectivity in new chemical transformations. The significance of this work lies in its application to synthesis. Particular attention is given to bioactive natural products with interesting molecular architecture, wherein the objective is to develop efficient synthetic strategies that facilitate extensive structural modifications to probe biological activity. Students in our group will be exposed to the vast repertoire of reactions and learn the analytical skills to plan, execute and optimize reaction sequences.

Ever since the development of the Wacker Oxidation in 1959, countless groups have probed the usage of Pd to activate olefins for the construction of interesting and useful molecules. A key intermediate within these transformations arises from nucleopalladation of the alkene, which can be followed by reductive elimination to yield difunctionalized products. With a chiral ligand bound to Pd, these products can be chiral with potentially high ee. We are highly interested in such reactions both from inter- and intra-molecular substrates.

Palladium-catalyzed alkene difunctionalization

Previously, we have shown that we are able to asymmetrically dearomatize simple heterocyclic feedstocks such as quinoline (Pappopula et al, 2015) and pyrazine (Ketelboeter et al, 2024), using Cu-StackPhos bound acetylides. These are methodologies that create privileged scaffolds and help fill voids within the field of enantioselective dearomatization of heterocycles. We have a continued interest in expanding the scope of this chemistry in other new, creative ways.