An asymmetry induced azepine-ring formation through the ene reactions at the periphery of heterocyclic systems

Article abstract of DOI:10.1016/0040-4020(96)00773-9

The azepine-ring formation through the ene reactions proceeds in a concerted manner although the PM3 molecular orbital calculations of the model reactions suggests that the azepine-ring formation is constituted of two consecutive orbital-allowed reactions. Both imine and carbonyl ene reactions using the aldehydes bearing a chiral center at the alkenylamino moiety have performed a self-immolating chirality transfer to the azepine ring.