ORGN 329 |
| Inspired by Nature's ability to generate carbonyl anions by utilizing thiamin diphosphate containing enzymes, we are developing and extending this process to form new carbon-carbon bonds. A new biomimetic carbonyl anion reaction catalyzed by heterothiazolium-derived carbenes that is fully operative under neutral aqueous conditions will be presented. The combination of keto carboxylates and thiazolium-derived zwitterions produces reactive carbonyl anions in a buffered protic environment that readily undergo conjugate additions to unsaturated electrophiles in high yield. In this process, no benzoin products from carbonyl anion dimerization are observed. The scope, mechanistic attributes of the process, and future directions will be discussed.
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New Reactions and Methodology
1:00 PM-5:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Ballroom B, Oral
Division of Organic Chemistry |
