Regioselectivity on the reactions of alpha,beta -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-dimelhylcyclohexen-1-one and acyclic alpha,beta -enones afforded 1,2-addition products. (C) 2000 Elsevier Science Ltd. All rights reserved.