We successfully expand the application of lactols or cyclic hemiaminals as nucleophiles for the asymmetric synthesis of both N,O- and N,N-acetal moieties contained in the structure of ring-fused piperidine derivatives. This efficient one-pot protocol involves an organocatalyzed asymmetric aza-Diels–Alder reaction and iminium ion induced cyclization sequence to ultimately deliver heterocyclic compounds with excellent stereoselectivity in high yield, containing three continuous stereogenic centers.