Highly regioselective synthesis of substituted tetrahydroquinolines by palladium-catalyzed cyclization of substituted 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene

The reaction of 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene in the presence of a palladium catalyst is described. Substituted tetrahydroquinolines having a vinyl group at the 3- or 2-position were synthesized, in which the regioselectivities of the double allylic substitution reactions have been altered depending on the substituent on the amino group.