Asymmetric reactions merging organocatalysis and metal catalysis significantly broaden the scope of organic synthesis.N evertheless,t he accomplishment of stereoselective annulations combining two types of dipole species,i ndependently generated from the activations of organocatalysts and metal complexes,s till remains as ac hallenging task. Now, Morita-Baylis-Hillman carbonates from isatins and carbamate-functionalized allyl carbonates could be chemoselectively activated by achiral Lewis basic tertiary amines and chiral iridium complexes.T he zwitterionic allylic ylides and 1,4-pallyliridium dipoles formed in situ are assembled in ah ighly stereoselective [4+ +3] annulation pattern. Similar cooperative catalytic strategy could be applied for the reactions of Morita-Baylis-Hillman carbonates and vinyl aziridines,furnishing an asymmetric [3+ +3] annulation reaction also with excellent stereocontrol. Scheme 1. Lewis base and transition-metal activations trategies for MBH derivatives and cooperative catalysis.