Catalytic Asymmetric Construction of a 1,2,4-Benzotriazepine Skeleton via Diastereo- and Enantioselective Decarboxylative [4+3] Cyclization

We have developed a protocol for palladium-catalyzed decarboxylative [4 + 3] cycloaddition reactions between 4-vinyl benzoxazinanones and azomethine imines to generate moderate to good yields of structurally diverse 1,2,4-benzotriazepines bearing two stereogenic centers with good to excellent stereoselectivities. This protocol not only addresses the challenge of asymmetrically constructing compounds with a 1,2,4-benzotriazepine skeleton but also demonstrates the utility of decarboxylative cycloadditions for the synthesis of enantioenriched polycyclic compounds.

Automated summary

A new protocol has been developed for the asymmetric construction of compounds with 1,2,4-benzotriazepine skeleton, demonstrating the utility of decarboxylative cycloadditions for the synthesis of enantioenriched polycyclic compounds. The reaction yields moderate to good results with good to excellent stereoselectivities.