Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines

Relatively unstable cyclic imines, generated in situ from their corresponding alicyclic amines via oxidation of their lithium amides with simple ketone oxidants, engage aryllithium compounds containing a leaving group on an ortho-methylene functionality to provide polycyclic isoindolines in a single operation. The scope of this transformation includes pyrrolidine, piperidine, azepane, azocane, and piperazines.

Automated summary

Relatively unstable cyclic imines, generated from alicyclic amines via oxidation of their lithium amides with simple ketone oxidants, react with aryllithium compounds containing a leaving group on an ortho-methylene functionality to form polycyclic isoindolines in a single step. The transformation can be applied to pyrrolidine, piperidine, azepane, azocane, and piperazine.