REGIOSELECTIVE REACTIONS OF ENAMINONES WITH ENONES-II. INTRAMOLECULAR REARRANGEMENTS INVOLVING CARBON TO OXYGEN ACYL MIGRATIONS

Article abstract of DOI:10.1016/0040-4020(82)80202-0

Intramolecular dynamic behaviour helps in predicting the regioselectivity of reactions in ambident molecules.Thus the enaminones (1) react on the C-2 carbon atom with benzoquinone.Reaction proceeds with an intramolecular acyl shift following formation of the initial reaction complex upon reaction at position C-2 of the enaminone and the quinone.Under certain conditions the reaction is regiospecific and proceeds stereospecifically.