CAREER: Catalyst-controlled Activation of Oxaziridines

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This project addresses the Lewis acid activation of oxaziridines as a unified platform for the discovery of a range of new stereoselective catalytic oxidative methods. Lewis acid catalysis is a new approach to the development of oxidative transformations and will be applicable to the study of a variety of oxidants (e.g., dioxiranes, peroxyacids, hypervalent iodine). Fundamentally new oxaziridine reactivity will be developed, including highly regioselective aminohydroxylation reactions. Mechanistic studies will provide a deeper insight into the unique electronic structure and oxenoid reactivity of oxaziridines. Regioselective asymmetric alkane oxidation will also be explored, addressing a long-standing challenge in organic synthesis. Communication skills training will be integrated into the chemistry curriculum at both the undergraduate and graduate level by (1) integrating peer evaluation of our student seminars into the graduate chemistry curriculum, and (2) introducing blogs as coursework in an advanced undergraduate laboratory course.With the support of this CAREER award from the Organic and Macromolecular Chemistry Program, Professor Tehshik P. Yoon, of the Department of Chemistry at the University of Wisconsin, is developing new reactions applicable to the controlled and efficient synthesis of complex organic molecules. Although oxidations are a fundamental class of reactions capable of increasing functionality and molecular complexity in organic compounds, only a limited number of complexity-building oxidative transformations can be achieved using known methods of enantioselective catalysis. Professor Yoon and his students are developing a general strategy for the catalysis of broad classes of oxidation reactions. These studies are addressing long-standing problems in organic synthesis and are expected to lead to new and efficient methods for chemical synthesis. As part of a comprehensive strategy to better prepare both graduate and undergraduate students for careers at the forefront of the chemistry professions, Professor Yoon will integrate communication skills training into the chemistry curriculum, introducing peer review of student seminars and blogs as coursework in an advanced undergraduate laboratory course.