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Leveraging Electron-Deficient Iminium Intermediates in a General Synthesis of Valuable Amines.

ABSTRACT: The development of reactions converting alkenes and alkynes into valuable building blocks remains one of the main goals of synthetic chemistry. Herein, we present the leveraging of highly electron-deficient iminium ions, rare and fleeting intermediates, into a general amine synthesis. This enables the preparation of amines bearing e.g. valuable α-trifluoromethyl moieties under mild conditions. This broad concept is highlighted by the late-stage amination of quinine into a biologically interesting new analogue.

SUBMITTER: Hsu CS

PROVIDER: S-EPMC9311413 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Leveraging Electron-Deficient Iminium Intermediates in a General Synthesis of Valuable Amines.

Hsu Che-Sheng CS Gonçalves Carlos R CR Tona Veronica V Pons Amandine A Kaiser Marcel M Maulide Nuno N

Angewandte Chemie (International ed. in English) 20220316 20

The development of reactions converting alkenes and alkynes into valuable building blocks remains one of the main goals of synthetic chemistry. Herein, we present the leveraging of highly electron-deficient iminium ions, rare and fleeting intermediates, into a general amine synthesis. This enables the preparation of amines bearing e.g. valuable α-trifluoromethyl moieties under mild conditions. This broad concept is highlighted by the late-stage amination of quinine into a biologically interestin ...[more]

PMID: 35103377

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