Studies on the reactions of α,β-enones with allyl indium reagent; effects of TMSCl as promoter on regioselectivity

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.