March 4, 2011

Anodic Coupling Reactions: Exploring the Generality of Curtin−Hammett Controlled Reactions

Alison Redden and Kevin D. Moeller

Org. Lett., 2011, 13 (7), 1678–1681

Intramolecular anodic olefin coupling reactions can be compatible with the presence of dithioketal protecting groups even though the dithioketal oxidizes at a lower potential than either of the groups participating in the cyclization. In such cases, product formation is controlled by the Curtin−Hammett Principle. In this study, the generality of such reactions is examined along with the use of alternative reaction conditions to suppress unwanted side reactions.