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ABSTRACTA new method for the stereoselective synthesis of substituted tetrahydrofurans or pyrrolidines via Pd-catalyzed reactions of gamma-hydroxy or gamma-amino alkenes with aryl or alkenyl halides will be described. These reactions form both a carbon-carbon and a carbon-heteroatom bond in a single transformation, generating up to two stereocenters in one step with diastereoselectivities of up to >20:1. Mechanistic studies suggest the reactions proceed via the intramolecular syn-insertion of an olefin into an intermediate Pd(Ar)(OR) or Pd(Ar)(NRR?) complex. The structure of the Pd-catalyst has a dramatic influence on the relative rates of several competing mechanistic pathways, which allows for the selective synthesis of several structurally different heterocyclic products from identical precursors by changing the catalyst. The scope and limitations of this methodology will be discussed, along with other applications such as the use of these reactions for the construction of pyrazolidines, isoxazolidines, imidazolidin-2-ones, and, piperazines. Applications towards the synthesis of biologically active molecules will also be described.
BIOGRAPHICAL SKETCH:John P. Wolfe was born in Greeley, Colo., and received his B.A. degree from the University of Colorado, Boulder in 1994. As an undergraduate he conducted research in the labs of Professor Gary A. Molander. He received his Ph.D. degree in 1999 from the Massachusetts Institute of Technology under the guidance of Professor Stephen L. Buchwald. Following the completion of his Ph.D. studies, he spent three years as an NIH postdoctoral fellow in the lab of Professor Larry E. Overman at the University of California, Irvine. He joined the faculty at the University of Michigan in July, 2002, where he is currently an Associate Professor of Chemistry. Professor Wolfe?s current research is directed towards the development of new palladium-catalyzed reactions for the stereoselective synthesis of heterocycles, and studies of alkene insertion processes of late transition metal alkoxide and amido complexes. Other research interests include the development of new tandem reactions, and the total synthesis of biologically active natural products. His research accomplishments have been recognized with several awards, including the Dreyfus New Faculty Award (2002), the Research Corporation Innovation Award (2002), the 3M Untenured Faculty Award (2003-2005), the Amgen Young Investigator Award (2004), the Lilly Grantee Award (2005), the Camille Dreyfus Teacher-Scholar Award (2006), and the GlaxoSmithKline Scholar Award (2008-2009).
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