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A series of monocyclic and bicyclic heterocycles with exocyclic alkenes were constructed in a stereoselective fashion by an organozinc/Ni(COD) 2 - mediated cyclization of alkynyl enones. Both reductive and alkylative cyclization manifolds were accessible depending on the ligand and organozinc structure. Alkylative cyclizations were generally more efficient than reductive cyclizations, particularly with cyclic substrates.