New Concepts for Multifunctional Asymmetric Catalysis

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With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, Professor Daniel Seidel of the Department of Chemistry at the University of Florida is studying new methods for asymmetric catalysis, particularly in the important area of chiral Brønsted acid catalysis. The ability to prepare complex chiral molecules in the most cost-effective way possible is directly dependent on the availability of sustainable synthetic methodologies. The new synthetic methods being explored and developed in this work have the potential to provide improved access to important compounds such as polycyclic ethers and lactams, with potential applications in the chemical and pharmaceutical industries, as well as throughout academia. Furthermore, this project provides an ideal training ground to prepare the next generation of researchers in the chemical sciences. Undergraduate students from different institutions will participate in the planned activities.This project aims to advance the field of asymmetric catalysis on a fundamental level through exploration of conceptually new and underdeveloped methods of substrate activation. A major goal is the development of reactions that produce enantiomerically enriched products through intervention of chiral ion pairs. Novel Brønsted acids and hydrogen bond donor catalysts will be explored to facilitate unprecedented enantioselective processes and address challenging synthetic problems. There is real room for innovation in this area as most such chiral Brønsted acid catalysts studied heretofore are based upon now familiar BINOL-phosphate frameworks. A focus is on reactions that proceed via the intermediacy of highly reactive oxocarbenium ions and related species. Multifunctional catalysts are being developed with the goal of achieveing enzyme-like catalysis and enantioselectivity under mild reaction conditions.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.