Ketenes serve as versatile synthons in organic chemistry due to their distinctive physical properties and exceptional chemical reactivity. The asymmetric cyclization of ketenes has emerged as a powerful strategy for the efficient construction of chiral heterocyclic scaffolds. In contrast to conventional synthetic approaches, the photoinduced Wolff rearrangement of α-diazoketones offers a milder and more sustainable alternative for the traceless generation of ketenes. This chapter summarizes recent advances in the asymmetric cyclization of photogenerated ketenes via transition metal catalysis and organocatalysis, with particular emphasis on the underlying mechanisms and stereochemical control. In particular, the mild photochemical conditions that allow for the traceless and transient formation of ketenes via Wolff rearrangement are critical to the success of these cyclization reactions.