Asymmetric C(sp3)–H functionalization has emerged as a useful tool for simultaneous installation of functionality and chirality onto hydrocarbon units. Stereodiscrimination in reactions between a strong C(sp3)–H bond and a prochiral substrate, potentially forging vicinal stereogenic centers in a single step, however, remains a significant challenge. We report here a photocatalytic diastereo- and enantioselective C(sp3)–H functionalization/intramolecular cyclization reaction.