CAREER: Strategic Advancement of Chemical Theory and Computations towards Complex Synthetic Transformations

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In this CAREER award funded by the Chemical Catalysis program of the Chemistry Division, Professor (Paul) Ha-Yeon Cheong of Oregon State University is developing new software methods for applying computational chemistry to study reactions that form complex compounds useful for pharmaceutical technology and the study of biochemical processes. Many catalytic reactions are important for the synthesis of molecules that display useful pharmacological or biological properties; however, it is often a challenge to devise experimental methods to define the fundamental details of how these reactions proceed. Very often, computational methods can be used to provide such deeper insights. In this research project, new software and computational methods are being developed to improve the level of detail at which a catalytic reaction can be studied. The longer range impacts of such work would be to allow the chemist to use a computer to design a catalytic reaction to make a specific product, thus saving the time and expense of performing preliminary laboratory work. Professor Cheong's research project is expanding the reach of computations and theory towards the efficient elucidation of mechanisms and factors that control the reactivity and selectivity of chemical transformations involving structures with significant conformational flexibility and where the interactions responsible for the reactivity and selectivity are largely non-covalent, weak, and/or complex. Specifically, Professor Cheong is developing theoretical tools and applying these methods in order to determine the central factors that determine the mechanism and the stereoselectivity of: (i) site-selective desymmetrization of cis-1,2-diols by scaffolding organic catalysts; (ii) kinetic resolution of beta-amino alcohols by beta-hairpin peptide-catalyzed acylation, and (iii) phosphine-catalyzed nucleophilic coupling of allenoates. Ultimately, this line of research will inform experimentalists with an intuitive understanding of the key factors in order to design better reactions and processes. The developed software platform and the scientific discoveries are being shared with the public and experts alike via an online gallery. An introductory undergraduate course in academic and career development for students planning for a career in science and technology is being offered at the university. Finally, a student organization has been created where the goal is to provide peer mentorship and support structures between student peers across the post-secondary education strata.