Synthesis, Mechanistic Investigations, and Applications of Transition Metal Enolates for Asymmetric Synthesis

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Brian M. Stoltz of the Division of Chemistry and Chemical Engineering at the California Institute of Technology will investigate the origins of high enantioselectivity in an important asymmetric catalytic alkylation reaction discovered in his laboratory, and apply the knowledge gained toward the development of a broad platform for enantioselective transition metal enolate functionalization chemistry. The work described could provide unprecedented access to simple chemical building-blocks containing stereogenic centers, and could be widely adopted by synthetic chemists in both academia and industry. This unique collection of tools could enable chemists to push beyond the state-of-the-art in applying such technologies to compounds and substances that are beyond the scope of the current methods. In addition to the on-site, laboratory science described in this grant, the science proposed herein will directly impact the education of scientists at the California Institute of Technology, while the skill set and expertise they gain will broadly impact society-at-large as they too move on to productive careers in academia, industry, and government. Finally, ongoing teaching and outreach efforts with young students (K-6) will impact the lives and decisions of the next generation of students.