ORGN 273 |
| Ring-closing metathesis of olefins substituted with both electron-withdrawing and electron-donating groups has been investigated. In case of α-alkoxy-acrylates RCM proceeded readily resulting in the corresponding oxygen heterocycles. Besides the investigation of different model systems, this methodology has been applied to more elaborate substrates. Thus, the highly oxygenated biologically important sugars KDO and DAH were synthesized in very efficient and short procedures, as well as a series of derivatives. Finally, we also showed that functionalized dehydroamino acids undergo RCM in a successful manner, giving rise to the corresponding cyclic enamides. This concept was applied in a synthetic route to pharmaceutically relevant 4-alkylpipecolic acids.
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Metal-Mediated Reactions and Syntheses
1:00 PM-5:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- 202B, Oral
Division of Organic Chemistry |
