Long range activation of a sulfonyl dienophile via its oxosulfoxonium ion
Abstract
Complexation fo BF3 etherate to the epoxide oxygen of sulfone 1 triggers a reaction cascade that transforms the unreactive dienophile 1 into a diastereoisomeric pair of reactive oxosulfoxonium salts(γ-sultinium ions 6 and 7), corresponding to an activation occurring at five-bond distance from the reactive site.