Regioselectivity on the reactions of α, β-enones with allyl indium reagents in the presence of TMSCl was systematically studied. 2-Cyclohexen-1-one,(R)-carvone, 2-cyclohepten-1-one and chalcone produced 1, 4-addition products in good yields, whereas 2-cyclopenten-1- one, 2-methylcyclopenten-1-one, 4, 4-dimethylcyclohexen-1-one and acyclic α, β-enones afforded 1, 2-addition products.