The development of efficient methodologies for the synthesis of chiral organocatalysts remains a pivotal challenge in modern organic chemistry due to their widespread application in enantioselective synthesis. This study aims to explore novel pathways that utilize transition metal catalysis to achieve high enantioselectivity and yield. We employed an array of transition metal complexes to catalyze the reaction of prochiral substrates, optimizing conditions to ascertain the most effective catalyst systems. Our findings reveal that the use of a palladium-based catalyst with a nitrogen-containing ligand framework afforded the highest enantioselectivity and catalytic turnover number. Detailed mechanistic studies suggest that the ligand framework plays a crucial role in facilitating the chiral induction process. Furthermore, the reaction conditions were refined to minimize by-product formation and maximize atom economy. Conclusively, our approach presents a versatile and sustainable route to chiral organocatalysts, with potential implications for broadening the scope of organocatalytic reactions in pharmaceutical synthesis.