ORGN 459 |
| Nitrogen heterocycles are ubiquitous structures present in many natural products and other biologically active compounds. Although many methods have been developed for the synthesis of these molecules, few transformations have been achieved that effect ring-closure of an acyclic starting material with concomitant formation of a C1' carbon-carbon bond. This presentation describes a new approach to the stereoselective synthesis of N-protected pyrrolidines via the palladium-catalyzed carboamination of N-boc- or N-acyl-gamma-aminoalkenes with aryl bromides. These transformations lead to the formation of both C-N and a C-C bond, and afford the substituted pyrrolidine products in good yields with high diastereoselectivity (up to >20:1). Application of the methodology to the stereoselective synthesis of the biologically active natural product Preussin will also be presented along with the facile preparation of analogs of the natural product. |
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Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- C302, Oral
Division of Organic Chemistry |