An efficient iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters with amines has been developed. A range of functionalized β-homoproline amide derivatives were prepared via an iminyl radical-mediated intramolecular 1,5-cyclization followed by carbon radical-triggered intermolecular carbonylation. Examples on further transforming the obtained product were successfully discussed as well.