Cooperative Tertiary Amine/Chiral Iridium Complex Catalyzed Asymmetric [4+3] and [3+3] Annulation Reactions.

Author(s) Chen, Y.C.; Chen, Z.C.; Chen, Z.; Yang, Z.H.; Guo, L.; Du, W.
Journal Angew Chem Int Ed Engl
Date Published 2019 Aug 14
Abstract

Asymmetric reactions merging organocatalysis and metal catalysis significantly broaden the organic synthesis. Nevertheless, the accomplishment of stereoselective annulations combining two types of dipole species, independently generated from the activations of organocatalysts and metal complexes, still remains as a challenging task. Here we report that 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, respectively. Thus, the in situ formed zwitterionic allylic ylides and 1,4-π-allyliridium dipoles are finely assembled in a highly 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.

DOI 10.1002/anie.201907797
ISSN 1521-3773
Citation Chen Y-, Chen Z-, Chen Z, Yang Z-, Guo L, Du W. Cooperative Tertiary Amine/Chiral Iridium Complex Catalyzed Asymmetric [4+3] and [3+3] Annulation Reactions. Angew Chem Int Ed Engl. 2019.

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