New Methods for Asymmetric Synthesis of Valuable Chemicals

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The focus of this research is the development of methodology for the construction of a variety of C-X bonds: C-C, C-N and C-O. The majority of the effort will be be spent developing methods for catalytic asymmetric activation of alkenes for attack by non-metal bound, external nucleophiles. To this end, the synthesis of a variety of novel planar chiral Pd(II) catalysts will be carried out. The reactions targeted for catalysis include allylic imidate rearrangements, Cope and Claisen rearrangements, allylic ester rearrangements and cyclizations to form chiral nitrogen and oxygen containing heterocycles. A second aspect of the research focuses on the asymmetric Heck reaction. The objective of all of the investigations is to develop practical catalytic methods through systematic studies that will provide fundamental insight that will enable future rational development of new asymmetric catalyst architectures. With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Larry E. Overman of the Department of Chemistry at the University of California, Irvine. Professor Overman will focus his work on developing new catalytic asymmetric transformations of inexpensive alkenes to valuable enantiopure products. The development of this type of methodology is of great importance to the pharmaceutical industry.