Asymmetric Catalysis with Ligated Copper Hydride

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This project is focused on the theme of catalysis, specifically involving copper(I) hydrido complexes that are mainly ligated by nonracemic bis-phosphines ((L*)CuH). The action of catalytic (L*)CuH on aryl ketone intermediates will form products useful for the synthesis of known pharmaceuticals. Catalytic (L*)CuH will be used in new contexts that will afford valued nonracemic intermediates for synthesis, extending the limits of this CuH chemistry. A newly designed ligand will be synthesized to test the factors that may control both reaction rates and enantioselectivities. Experiments aimed at investigating the nature of the species (L*)CuH are planned, supporting the goal of providing a practical source of (L*)CuH; i.e., effectively CuH in a Bottle. Using boranes as the stoichiometric source of hydride, new inroads to boron enolates will be developed and used to synthetic advantage based on transmetalations. Finally, copper-in-charcoal (Cu/C) will be explored as a potential new approach to asymmetric (heterogeneous) organocopper chemistry.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Bruce H. Lipshutz of the Department of Chemistry and Biochemistry at the University of California at Santa Barbara. Catalysis represents a powerful tool in the development of more economical and environmentally friendly technologies. Professor Lipshutz and his students are exploring new ways to catalyze organic chemical transformations using copper compounds. These copper compounds are significantly less expensive than the more commonly used precious metal catalysts and offer unique chemical reactivity as well. By developing these new catalysts, Professor Lipshutz is developing methodologies that may be generally and broadly applicable in the synthesis of complex organic molecules and pharmaceuticals.