Allenes represent a distinctive class of organic molecules characterized by their unique physical and chemical properties. Among them, chiral allenes play a significant role in modern chemistry. They not only serve as pivotal frameworks for natural products and drug molecules but also are essential building blocks in organic synthesis. Over the years, numerous remarkable and efficient methods have been developed for the synthesis of chiral allenes. Notably, the catalytic synthesis of chiral allenes using transition metals in conjunction with chiral ligands has garnered considerable attention. This review paper aims to provide an overview of recent advancements in the synthesis of chiral allenes through asymmetric 1,4-difunctionalization of 1,3-enynes, in which two distinct strategies including non-radical and radical processes are highlighted.