Reactions of Tröger’s Base Derivatives with Aryne Intermediates

Reaction of rac-Tröger's base (TB) with aryl halides is described via ring opening with concomitant N-arylation in the presence of the t-BuOK/DMSO reagent system. The methylene bridge of the Tröger's base derivatives is eliminated by an aryne intermediate formed in situ, leading to the generation of N-arylated product in up to 67% yield. The reaction scope has also been extended to synthesize an enantiopure compound involving the rearrangement of the methylene bridge.