Substrate-controlled switchable asymmetric annulations of Morita–Baylis–Hillman carbonates from isatins and α-cyano-α,β-unsaturated ketones catalysed by cinchona-derived tertiary amines, giving tetrahydrofuro[2′,3′:4,5]pyrano[2,3-b]indoles or spirooxindoles incorporating a cyclopentene motif, were disclosed.