Abstract
A DBU promoted ring opening of donor-acceptor (D-A) cyclopropanes and sequential [3 + 2] annulation reaction with diversified 3-phenacylidene-2-oxindoles were reported. This facile protocol provided an efficient functional group controlled approach towards a variety of spiro [cyclopentane-1,3′-indoline]-2,2-dicarbonitriles (17 examples) and spiro [cyclopent [2]ene-1,3′-indoline]-3-carbonitriles (14 examples) derivatives with high yield. Mechanistic study suggests regioselective conjugate addition with varying functional groups, which control the reaction pathways. The advantages of good diastereoselectivity and wide substrate scope make this process highly attractive.
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