Radical cascade cyclization reactions provide an efficient method for the construction of polycyclic architectures with multiple stereogenic centers. However, achieving enantioselectivity control of this type of reaction is a challenging task. Here, we report an enantioselective cyclization of polyfunctional aryl cyclopropyl ketone and alkyne units, wherein the stereochemical outcome is directed by a chiral Ti(salen) catalyst. This transformation was proposed to proceed via a radical cascade process involving the reductive ring-opening of the cyclopropyl ketone followed by two annulation events entailing cyclization of the ensuing alkyl radical onto the alkyne and subsequent addition of the incipient vinyl radical to the Ti(IV)-enolate.