August 28, 2001

Anodic Cyclization Reactions: Reversing the Polarity of Ketene Dithioacetal Groups

Yongmao Sun, Bin Liu, Jeff Kao, D. Andre’ d’Avignon, and Kevin D. Moeller
Org. Lett., 2001, 3 (11), 1729–1732

Intramolecular coupling reactions of ketene dithioacetal groups with enol ether and alcohol nucleophiles have been studied. The reactions were initiated by an anodic oxidation of the ketene dithioacetal and proved to be compatible with the formation of five- or six-member rings, as well as the stereoselective generation of quaternary carbons.