ORGN 190 |
| Cyclopropanes have played a diverse role in organic chemistry due to their strained structure, interesting bonding characteristics, and value as internal mechanistic probes. Moreover, the prevalence of cyclopropane containing compounds with biological activity, whether isolated from natural sources or rationally designed pharmaceutical agents, has inspired chemists to find novel and diverse approaches to their synthesis. Over the last decade, our program has led to the development of several methods for the selective preparation of non-racemic, diastereomerically pure 1,2-disubstituted and 1,2,3-trisubstituted cyclopropanes. The strategy has its foundation in the classic homoallylic cation rearrangement but has also provided a forum for new mechanistic investigations. Our most recent efforts include the preparation of cyclopropanes from homoallylic sulfonates activated by benzyl and allylic substitution. Results of these investigations as well as related mechanistic issues will be presented.
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New Reactions and Methodology
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C301, Oral
Division of Organic Chemistry |
