An unprecedented chiral secondary amine-catalyzed[3 + 3]annulation of isatin N,N'-cyclic azomethine imines with α,β-unsaturated aldehydes was developed.This strategy allowed the construction of structurally novel spiro N-heterocyclic oxindole derivatives in good yields (up to 91％) and good to excellent enantioselectivities (up to ＞99％ ee),albeit with modest diastereoselectivities (up to 3.1∶1 dr).