An unprecedented N-heterocyclic carbene-catalyzed annulation of isatin-derived enals and o-hydroxyphenyl-substituted p-quinone methides as bifunctional reagents has been discovered. The new protocol involves a 1,6-addition of the homoenolate equivalent intermediates to the hydroxy donor-1,6-Michael acceptors and leads to spirocyclic oxindole-ε-lactones in high yields and very good stereoselectivities.