In recent years, asymmetric ring-opening reactions of epoxides have emerged as a compelling strategy for constructing chiral building blocks in organic synthesis. Among these, transition-metal-catalyzed stereoselective transformations of epoxides have garnered particular attention for their high efficiency and cost-effectiveness. The increasing interest and advancements in this area have spurred exploration into diverse transition metal catalysts and chiral ligands, highlighting their potential to facilitate a wide range of transformations with enhanced efficiency and flexibility. This review showcases significant achievements in transition-metal-catalyzed enantioconvergent transformations of epoxides, emphasizing their application scope and reaction mechanism.