September 23, 2008

Intramolecular Anodic Olefin Coupling Reactions: The Use of a Nitrogen Trapping Group

Hai-Chao Xu and Kevin D. Moeller*

J. Am. Chem. Soc., 2008, 130 (41), pp 13542–13543

Anodic olefin coupling reactions using a tosylamine trapping group have been studied. The cyclizations are favored by the use of a less-polar radical cation and more basic reaction conditions. The most significant factor for obtaining good yields of cyclic product is the use of the more basic reaction conditions. The cyclizations allow for the rapid synthesis of substituted proline derivatives.