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

ABSTRACT: 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.

SUBMITTER: Paul A 

PROVIDER: S-EPMC9039734 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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

Paul Anirudra A   Vasseur Camille C   Daniel Scott D SD   Seidel Daniel D  

Organic letters 20220131 5

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 <i>ortho</i>-methylene functionality to provide polycyclic isoindolines in a single operation. The scope of this transformation includes pyrrolidine, piperidine, azepane, azocane, and piperazines. ...[more]

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