CAREER: Synthesis and Study of Organic Silanols for Asymmetric Catalysis

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This award is funded under the American Recovery and Reinvestment Act of 2009 (Public Law 111-5). This project will design and develop new catalysts for asymmetric synthesis based on the hydrogen-bonding capabilities of silanols. While silicon is the second most abundant element on earth, present in various forms of inorganic silicates, the synthesis of chiral silanols is under-developed and the properties of organic silanols have never been examined for hydrogen-bonding catalysis. The development of metal-free catalysts is important because they tend to be non-toxic, cheap, moisture- and air-stable, simple to use, and capable of catalyzing a broad range of organic reactions. New chiral organic silanols will be synthesized and examined for the stereoselective formation of C-C bonds. Structural and computational studies will be performed to elucidate the mechanism of activation and asymmetric induction. Mechanistic studies will contribute to fundamental insight into hydrogen-bonding structure and function, and provide opportunities for hypothesis driven catalyst design. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Annaliese K. Franz of the Department of Chemistry at University of California, Davis. Professor Franz's research efforts revolve around the development of new silicon-based chiral materials and catalysts. Such chemistry will contribute to environmentally benign methods for chemical synthesis by developing metal-free catalysts that mini¬mize the use of reagents and organic solvents, increase efficiency, and approach 100% selectivity. Successful development of new catalysts will have an impact on the synthesis of chiral organic molecules in the pharmaceutical and agricultural industries. The proposed research program also integrates research training with science communication training and outreach to improve communication with the media, policymakers and the public that will increase awareness of how research is performed, ensure sound public policy, and inspire future scientists.