RUI: Catalyst Systems to Effect Asymmetric Induction in the Hydroamination of Olefins

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The Chemical Catalysis Program of the Chemistry Division supports the research project by Professor Wenzel. Professor Wenzel is a faculty member at the W. M. Keck Science Department at Claremont McKenna College. She is developing new molecules to catalyze selective hydroamination of alkenes. Hydroamination reactions are an efficient route for the preparation of amines, a common structure found in pharmaceutical and agrichemical products. The reactions are focused on making the synthesis sustainable. The catalyst molecules are designed to be readily available and to support robust reactions. The study is uncovering a wealth of fundamental information regarding the factors governing reaction design. The research is conducted entirely by undergraduate students. Professor Wenzel's program is well-poised to address the ongoing deficiency of underrepresented groups in science. She has an excellent record in training underrepresented minority students and successfully encouraging them to pursue graduate studies in chemistry. This research outlines the preparation of chiral heterodonor phosphorous/thioether (P/S) and phosphorous/amine (P/N) ligands as alternatives to classically-used bisphosphines for coordination onto palladium, ruthenium, and copper. The chiral, bidentate ligands are equipped with strong and weak donor-heteroatom pairs (e.g., P/S or P/N) to utilize favorable electronics to strongly influence the stability and reactivity associated with stereochemistry-defining reaction intermediates. The new catalysts are evaluated in two types of hydroamination reactions: an intermolecular, asymmetric anti-Markovnikov hydroamination of unactivated olefins and the enantioselective, Markovnikov hydroamination of dienes to produce dihydroquinolines. It is through a robust program in the training of undergraduate researchers that Professor Wenzel tries to advance of science as well as the education of future science professionals.