CAREER: Stereoselective manipulation of unstabilized carbocations

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With this CAREER award, the Chemical Synthesis Program is supporting the research and educational efforts of Dr. Ryan A. Shenvi of the Department of Chemistry at the Scripps Research Institute. The focus of this research is to develop a new class of stereoselective nucleophilic displacement reactions that operate on isolated tertiary carbon centers through attack of unstabilized carbocationic contact ion pairs. This research fills a major methodological gap in chemical synthesis that has been recognized for nearly 100 years. Realization of the goals of this proposal would broadly impact the synthesis of challenging tert-alkyl-substituted chiral materials that are difficult or impossible to access by other methods. A successful outcome of the research proposed here entails the reaction of unstabilized carbocations and various nucleophiles with high chemo- and stereoselectivity, which has important consequences for the production of materials for the interfacing fields of biology, medicine, and physics.The key focus of this research is on the development of concise and scalable syntheses of therapeutically relevant molecules through the invention of new chemical reactions that allow a degree of complexity which has been unachievable through standard methods. The proposed research will potentially allow ready access to a number of important natural and unnatural products while reducing the number of steps and increasing the efficiency. The educational component of this grant involves curriculum development and outreach through the Scripps SURF program. This effort involves the development of a curriculum for high-school, undergraduate, and graduate education that articulates the scientific method in the context of organic chemistry research.