A sequence of reactions that include an iridium-catalyzed regio- and enantioselective allylic amination, the formation of an amide, a ruthenium-catalyzed ring-closing metathesis, and an intramolecular Heck reaction allows for the preparation of [3,3,1]- and [4,3,1]-bicyclic amides. The target compounds have a nitrogen atom at the bridgehead, a nonplanar amide moiety, and a stereogenic center at the one-carbon bridge. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.