Synthesis and reactivity of 1-sulfonylcyclooctatriazoles

Abstract

Strained eight-membered cyclic alkynes undergo rapid inverse electron demand cycloaddition with sulfonyl azides to give the corresponding 1-sulfonylcyclooctatriazoles in excellent yield. Treatment of these sulfonyltriazoles with a chiral rhodium(II) carboxylate catalyst prompted transannular C–H bond insertion in good yield and with excellent ee, or 1,2-H shift.