ABSTRACT α‐Chiral allylic amines represent a privileged structure in organic synthesis, catalysis, and other areas. Thus, the development of catalytic methods for straightforward and efficient construction of chiral allylic amines has been a longstanding interest in synthetic chemistry. In this context, transition‐metal‐catalyzed asymmetric carbon‐carbon cross‐coupling is evolving into an enabling and versatile platform for direct synthesis of α‐chiral allylic amines. Thus, this review provides a comprehensive overview of recent advances in this dynamic area, highlighting key catalytic strategies and mechanistic insights for catalytic C─C bond‐forming processes that underpin the streamlined synthesis of chiral allylic amine frameworks from easily available starting materials.