Organic Acids, Bases, Catalysts, and Anion Recognition Reagents

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In this project funded by the Chemical Structure, Dynamic & Mechanism B Program of the Chemistry Division, Professor Steven R. Kass of the Department of Chemistry at the University of Minnesota explores charge-enhanced acids, bases, hydrogen bond catalysts. The goal of this research is to develop new and useful catalysts, and obtain a better understanding of how these species operate to facilitate their development. More efficient catalysts are needed in the preparation of chemicals required in our daily life, such as the production of pharmaceuticals and polymers. This project lies at the interface of organic, physical, and analytical chemistry, and is particularly well suited for educating and training young scientists. Two patents have resulted from NSF-supported work in this group and a wealth of practical applications ranging from human health and the environment to agriculture and chemical industry may arise from this research.Charge-enhanced acids, bases, and hydrogen bond catalysts (salts) are being prepared and characterized. Their catalytic abilities are being examined in a variety of organic transformations, and structural variations are being probed to increase their reactivity. The role of covalent incorporation of the counterion at a remote location in these salt based catalysts are being studied. Chiral substrates (e.g., thioureas, binols, binol-derived phosphoric acids, and alkaloid bases) are being prepared and their enantioselectivities are being determined. Catalysts with chiral counterions for double stereodifferentiation are also being investigated.