A number of salen-metal complexes were prepared and their enantioselective catalytic properties toward the asymmetric iodolactonization of (E)-and (Z)-5-substituted-4-pentenoic acid derivatives were investigated. The catalyst system based on salen-Co(II) complex exhibited moderate to good enantioselectivity with the e.e. value ranging from 53% to 74%, as well as high regioselectivity of δ-vs. γ-iodolactones. The salen-Co(II) complex showed the highest enantioselectivity on the asymmetric iodolactonizations of (Z)-5-substituted-4-pentenoic acid derivatives among these reagent-controlled iodolactonization protocols known so far. A number of salen-metal complexes were prepared and their enantioselective catalytic properties toward the asymmetric iodolactonization of (E) -and (Z) -5-substituted-4-pentenoic acid derivatives were investigated. The catalyst system based on salen-Co ) complex exhibited moderate to good enantioselectivity with the ee value ranging from 53% to 74%, γ-iodolactones. The salen-Co (II) complex showed the highest enantioselectivity on the asymmetric iodolactonizations of (Z) -5-substituted-4-pentenoic acid derivatives among these reagent-controlled iodolactonization protocols known so far.