New Technologies Based on Organocopper Chemistry

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The main theme of this work is the use of copper (I) complexes to catalyze a variety of asymmetric organic reactions. Most of the proposed chemistry involves the catalytic use of asymmetrically ligated copper hydride or alkyl complexes. The copper hydrides will be used for asymmetric hydrosilylation of ketones and a 1,4-reducation-transmetallation protocol for converting alpha, beta unsaturated ketones into Z-boron enolates. The copper alkyl complexes will be used primarily for asymmetric 1,2 additions to aldehydes and to effect alkylative kinetic resolution of racemic epoxides.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Bruce H. Lipshutz of the Department of Chemistry at the University of California at Santa Barbara. Dr. Lipshutz will work on the development of copper complexes capable of catalyzing a number of chemical reactions. Most of these copper catalyzed carbon-hydrogen and carbon-carbon bond forming reactions produce molecules which are chiral (have two nonsuperimposable mirror images) and make only one of the two possible forms (a single enantiomer). Development of this family of reactions is one of the most important problems facing the pharmaceutical industry today. These transformations which are catalytic in copper may be amenable to large scale production of fine chemicals and pharmaceuticals. Students trained during the course of this work will gain skills needed by the pharmaceutical and speciality chemicals industries which now produce a number of single enantiomer compounds.