Chameleon-Like Activating Nature of the Spirooxindole Group in Donor-Acceptor Cyclopropanes.

The concept of a chameleon activating group is considered in the context of donor-acceptor cyclopropane chemistry. When spiro-conjugated with cyclopropane, oxindole can act as an acceptor or a donor depending on the electronic nature of vicinal substituents. This dichotomy is reflected in the alteration of chemoselectivity of spiro[oxindole-1,3'-cyclopropane] ring opening with nucleophiles.