Intramolecular Anodic Olefin Coupling Reactions

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With this award, the Organic and Macromolecular Chemistry Program supports the research of Professor Kevin D. Moeller of Washington University. This research project studies intramolecular anodic olefin coupling reactions, in which carbon-carbon bond formation occurs to afford cyclic products which retain functional group handles for further synthetic elaboration. Professor Moeller is exploiting this reactivity for the synthesis of angularly-fused triquinanes and related 5-6-5-fused ring systems (alliacol A). Analogous olefin-heteroatom couplings offer access to pyrrolidine rings, leading to synthesis of the immunosuppressant FR901483. Through the oxidation of chiral enolate equivalents and subsequent nucleophilic trapping of the resulting radical cations, Professor Moeller seeks asymmetric coupling reactions, while other studies address the reversal of polarity in intermolecular alkylation reactions and the development of new oxidative routes to heterocycles.Formation of carbon-carbon bonds represents one of the most critical requirements for the synthesis of complex organic molecules, and Professor Moeller is developing new methods to accomplish this. In his method, the driving force for carbon-carbon bond formation is provided by the removal of electrons from selected reactants. Although such oxidation reactions are often effected by a variety of chemical oxidants, Professor Moeller exploits electrochemical techniques, using equipment as simple as a 6-Volt lantern battery to carry out the desired transformations.