Chiral salen ligand is one of the most effective and popular classes of chiral ligands used in asymmetric synthesis. The study of this ligand is a vital and valuable area of research in organic chemistry, which is used for various metal-catalyzed asymmetric processes such as allylic oxidation [1]. Asymmetric allylic oxidation of cycloolefins and synthesis of chiral allylic esters is one of the most important reactions in asymmetric synthesis, which, unlike hydroxylation and epoxidation, forms a second functional group while the double bond remains unchanged [2-4]. An efficient chiral salen ligand and also various perester derivatives were synthesized and their structures were confirmed by 1H NMR and 13C NMR spectroscopic techniques. Finally, they were used in the Kharasch-Sosnovsky reaction for the synthesis of chiral allylic esters. Optimized condition for this reaction was achieved by changing some parameters such as temperature, solvents, amount of heterogeneous chiral ligand and amount of copper salt. Chiral allylic esters were obtained in good yields and moderate enantioselectivities.