September 13, 2010

Intramolecular Anodic Olefin Coupling Reactions: Use of the Reaction Rate to Control Substrate/Product Selectivity

Hai-Chao Xu and Kevin D. Moeller

Angew. Chem. Int. Ed. 2010, 49, 8004–8007

Look out—it’s a trap! The anodic coupling of olefins with amine trapping groups to form proline and pipecolic acid derivatives with a quaternary α carbon atom (see scheme) was successful despite the significantly lower oxidation potential of the product relative to that of either functional group in the substrate: owing to the very fast cyclization, the oxidation potential of the substrate is lower than that of the product.