ORGN 198 |
| A general protocol that achieves the union of aryl halides and divinyl or enyne carbinols to afford stereochemically defined tri- or tetrasubstituted olefins in good yields (up to 83%) has been developed. The mechanism by which this proceeds is believed to involve the intermediacy of a cyclopropanol, followed by a novel skeletal reorganization. The ability to suppress β-hydride elimination of organopalladium intermediates and the presence of a free hydroxyl functionality on the divinyl (or enyne) carbinol appears to be critical to the success of these processes. This reaction manifold provides the basis for a variety of novel ring expansion and annulation reactions.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
