We describe a Brønsted acid-catalysed cascade reaction consisting of a Wagner–Meerwein rearrangement and a subsequent intra- or intermolecular Friedel–Crafts reaction leading to adamantane-based heterocycles. In contrast to the reported W.–M. rearrangements, in this case an iminium moiety serves as the acceptor of a migrating nucleophilic alkyl group in a [1,2]-alkyl shift.