A visible-light-promoted protocol for azaspirocyclic synthesis from N-benzylacrylamides and alkyl chlorooxoacetates has been established. This cascade reaction proceeds through sequential free radical addition, cyclization, and dearomatization, enabling the convenient construction of key azaspirocyclic derivatives and the introduction of valuable ester groups in a single step. In addition, this transformation demonstrates broad substrate compatibility and high tolerance toward different functional groups, showcasing remarkable efficiency in functional group insertion and bond formation.