Professor Woerpel's research focuses on the development of new methodologies for the construction of carbocyclic and heterocyclic compounds through the (3+2) annulation reactions of functionalized allylsilanes. Use of allylsilanes with strategically-placed electron-donating substituents permits rapid 1,2-silyl migration in the initially formed beta-silyl carbocations, leading to more stable carbocations which then undergo annulation with a variety of reactive functionalities. In addition to providing synthetic access to a variety of cyclic structures, these studies also permit the assessment of the role of electronic factors in these annulation reactions. Portions of the research program are particularly designed to encourage participation by undergraduate research students. Professor Woerpel will also examine the effectiveness of new pedagogical tools for improving student comprehension of organic chemistry, focusing on three central themes, stereochemistry, conformational analysis and inductive effects in determining acidity. With this CAREER award, the Synthetic Organic Program supports the research and educational activities of Professor Keith A. Woerpel of the Department of Chemistry at the University of California, Irvine. Professor Woerpel's research efforts are focused on the development of new approaches for the synthesis of cyclic compounds. These studies, exploiting unique reactions of silicon-containing molecules, promise access to a variety of carbocyclic (containing only carbon) and heterocyclic compounds (containing elements such as nitrogen in addition to carbon). Such cyclic structures form the basis of numerous pharmaceutical compounds and other important products. Professor Woerpel's educational activities include the involvement of undergraduates, recruited both from his home campus and through outreach programs, in his research program. Professor Woerpel will also incorporate new laboratory- and computer-based approaches and implement a learning cycle approach to the teaching of undergraduate organic chemistry.
