Asymmetric Cascade Carbonylation/Annulation of Benzyl Bromides, CO, and Vinyl Benzoxazinanones Enabled by Pd/Chiral Lewis-Base Relay Catalysis

A highly enantioselective cascade carbonylation/annulation of benzyl bromides, CO, and vinyl benzoxazinanones under mild conditions has been established by Pd/chiral Lewis base relay catalysis, providing an efficient method to assemble chiral quinolinones from readily available starting materials in good yields with excellent diastereo-and enantioselectivities. The palladium catalyst plays two roles in this reaction, enabling both the carbonylation process and the generation of the zwitterionic pi-allyl palladium intermediate.

Automated summary

A highly enantioselective cascade carbonylation/annulation reaction has been established by Pd/chiral Lewis base relay catalysis, which assembles chiral quinolinones efficiently with excellent diastereo- and enantioselectivities from readily available starting materials under mild conditions. The palladium catalyst plays dual roles in this reaction, facilitating both the carbonylation process and the generation of the zwitterionic pi-allyl palladium intermediate.