A type of chiral salen complexes bearing Lewis acid, including FeCl3, AlCl3, ZnCl2, and SnCl4 has been synthesized. The prepared complexes proved to be reactive and enantioselective in the hydrolytic kinetic resolution of terminal epoxides. The catalysts could be recovered and reused several times with simple treatment after reaction, without loss of activity and enantioselectivity. (salen)Co(II) and Lewis acid in mol ratios of 1: 1, 1: 2, and 1: 3 showed the same activity, enatioselectivity, and stability. The characterization of the complexes in-situ generated by the reaction of (salen)Co(II) and Lewis acid in mol ratios of 1: 1, 1: 2, and 1: 3 in CH2Cl2 was performed by UV-Vis, which showed an identical spectrum and did not display any change along with the time prolonged. Thus, the present catalysts can be applicable for large scale processes for HKR reaction of racemic epoxides.