The Cs2CO3-mediated divergent [3 + 2] and [4 + 2] annulation of O-tosylhydroxylamines with 3-hydroxyoxindole has been disclosed, delivering various amino-substituted tetrahydrofuran and oxazinane spirooxindoles in moderate to good yields. The diastereoselective [3 + 2] annulation approach exhibits mild conditions and good substrate tolerance.