CAS: Catalytic Stereoselective Fragment Coupling Reactions of Feedstock Chemicals

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The development of new transformations that convert abundant chemical feedstocks efficiently into chiral molecules of biological importance is essential to the future advances in biology and medicine. In this project, Dr. Meek is developing catalytic, multicomponent carbon-carbon bond-forming reactions that link hydrocarbons with common molecular fragments. Such transformations provide an innovative strategy for synthesizing new complex molecules, in addition to providing economic and manufactural advantages over current methods. By using earth abundant transition metal catalysts, Dr. Meek and his team are demonstrating that readily available starting materials can be converted into synthetically-versatile, reactive intermediates to deliver very specific product structures with medical-relevance. Dr. Meek is actively engaged in outreach activities that build upon his research and focus on topics that demonstrate the enabling impact chemical synthesis and catalysis have on society. These activities, which include increasing participation of undergraduate students of all backgrounds and incorporating broad educational components into courses at various levels, are aimed towards enhancing all students’ STEM education and creating supportive environments for fostering next-generation scientists. This team also plans to integrate and expand their established outreach activities (e.g., AM-WISE, University of North Carolina (UNC) Science Expo, National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE), and their NSF-funded UNC Research Experiences for Undergraduates (REU)program).In this project, funded by the Chemical Synthesis Program of the Chemistry Division, Dr. Meek and his team of graduate and undergraduate students at the University of North Carolina at Chapel Hill, develop stereoselective nickel-catalyzed fragment coupling reactions of olefins. These transformations exhibit high levels of enantio- and diastereoselectivity essential for rendering the syntheses of difficult-to-access molecular entities substantially more time and cost effective – properties that are of importance to both academic and industrial synthetic chemistry. In general, these multicomponent processes involve the catalytic stereoselective generation of chiral nickel–alkyl species through an oxidative process, followed by coupling with a variety of carbon nucleophiles to afford a range of products. Reactions result in the formation of two new bonds and up to three new stereocenters, and allow for the generation of tertiary and quaternary stereocenters in addition to alcohol, amine, and carbonyl functionality. This research impacts areas of chiral ligand design and will stimulate areas of catalysis and method development with earth abundant transition metals. Dr. Meek is actively engaged in outreach activities that focus on enhancing students’ exposure to STEM education, increasing the participation of underrepresented groups in science, and broadening the dissemination of scientific knowledge.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.