CAREER: New Catalytic Reactions of Nitroxy Compounds

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In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor Oleg Larionov of The University of Texas at San Antonio is developing catalytic systems that can control the reactivity and stereoselectivity of nitroxy compounds. In particular, this work is seeking to provide fundamental insights into the interactions of transition-metal catalysts with highly reactive nitrosoalkenes, N-oxides and oxazines that are valuable precursors to alkaloids, many of which have important medicinal properties. The educational plan involves the development of a course focused on organic synthesis for graduate and advanced-level undergraduate students implementing process-oriented, guided-inquiry learning techniques. In addition, outreach efforts promote the ideas and principles of sustainable chemistry in the K-12 education by engaging local K-12 science teachers who are working with underserved populations. The chemistry of nitroxy compounds is distinguished by a diversity of chemical properties and reactivities. This unmatched diversity is a challenge for the development of synthetic methods exploiting unique reactivities of nitroxy compounds. In particular, control of regio- and stereoselectivity is a long-standing problem for these compounds. This study focuses on the fundamental factors that influence the regio- and stereochemical outcomes of cycloannulations and carbon-carbon bond-formation reactions of nitrosoalkenes, N-oxides, and oxazines. The catalytic reactions discovered in this project are expected to impact several adjacent research areas, including materials science, bioorganic chemistry and catalysis.