RUI: The Development and Application of Gold(I) Catalysts for Asymmetric Organic Transformations

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With this award from the Chemical Catalysis Program, Professor Anna G. Wenzel from the Claremont McKenna, Pitzer, and Scripps Colleges will explore catalytic methods in organic synthesis focusing on the design and development of new ligand systems for asymmetric gold(I) catalysis. She and her students will make use of the ability of gold to function as a carbophilic, soft Lewis acid to preferentially activate carbon-carbon multiple bonds in the presence of unprotected, Lewis-basic moieties, thereby allowing for the formation of new bonds via nucleophilic attack upon these activated substrates. The proposed research will examine a series of sulfur-based ligands for gold(I) catalysis. Once prepared, these gold(I) complexes will be investigated in two target reactions: the gold-catalyzed hydroamination of alkenes and an allenoate Claisen rearrangement. These reactions have been selected for their synthetic utility because they allow for atom-economical generation of valuable chiral reaction products.This work will address a growing demand for mild, selective, and sustainable synthetic routes for the preparation of organic compounds. Gold catalysts have the potential to fulfill this role in the preparation of pharmaceuticals, agrochemicals, and other materials. The proposed research addresses a fundamental need for readily available, "user friendly" catalysts. Students will have the opportunity to explore modern problems in synthetic chemistry and catalysis, while gaining practical training in laboratory techniques, problem-solving, presentation skills, and working as part of a team.