Annulation Reactions of Alpha-Substituted Allylsilanes

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The focus of this research involves the preparation of enantiomerically pure allylic silanes and the use of these compounds in annulation reactions for the production of five-and six-membered rings containing stereochemically defined tetrasubstituted carbons. The resulting compounds can serve as important intermediates for the synthesis of the natural products. This sequence will be used for the production of the natural product erythronolide A. Other studies will lead to the development of methodology for catalytic, enantioselective annulation reactions, for the preparation of cyclic peroxides, for the construction of 1,3-diamines, for annulations involving three-membered ring electrophiles and for the use of alpha-alkoxy allylic silanes in annulation reactions.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Keith A. Woerpel of the Department of Chemistry at the University of California-Irvine. Dr. Woerpel will focus his work on developing methodology for establishing stereochemistry at tetrasubstituted carbon atoms in five- and six-membered rings as well as in acyclic systems. These reactions will be applicable to the synthesis of complex, biologically active natural products and will thus have broader impacts in the pharmaceutical industry. The project also provides an excellent venue for the training of undergraduate, graduate and postgraduate students.