In this work the first H-bond-directed vinylogous iminium ion strategy has been developed as a convenient strategy for the γ,δ-functionalization of vinyl-substituted heteroaromatic aldehydes. Their reaction with α-mercaptoketones proceeds in a cascade manner involving 1,6-addition followed by intramolecular aldol reaction. Excellent stereoselectivities have been obtained as a result of the H-bond interactions controlling the outcome of the cyclization step. The application of the strategy for the synthesis of tricyclic compounds bearing furan, tetrahydrothiophene and dihydropyran moieties has also been demonstrated.