Acid-Promoted Carbosulfenylation of 1,6-Dienes: Selective Synthesis of Dehydropiperidines Scaffolds

An efficient method for the acid-catalyzed carbosulfenylation of 1,6-diene has been achieved employing N-(aryl/alkylthio)succinimides as a thiolating reagent. The reaction involves the generation of an episulfonium ion followed by intramolecular trapping with alkenes, which offers access to diverse thiolated dehydropiperidines in good yield. In addition, the synthesis of dihydropyran and cyclohexene derivatives, as well as the conversion of the arylthiol moiety to useful functional groups, were also demonstrated.