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Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.

ABSTRACT: The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we present a stereoselective α-amination of amides employing simple azides that proceeds under mild conditions with release of nitrogen gas. The amide is used as the limiting reagent, and through simple variation of the azide pattern, various differently substituted aminated products can be obtained. The reaction is fully chemoselective for amides even in the presence of esters or ketones and lends itself to preparation of optically enriched products.

SUBMITTER: Tona V

PROVIDER: S-EPMC4945995 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.

Tona Veronica V de la Torre Aurélien A Padmanaban Mohan M Ruider Stefan S González Leticia L Maulide Nuno N

Journal of the American Chemical Society 20160628 27

The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we present a stereoselective α-amination of amides employing simple azides that proceeds under mild conditions with release of nitrogen gas. The amide is used as the limiting reagent, and through simple variation of the azide pattern, various differently substituted aminated products can be obtained. The reaction is fully chemoselective for amides even in the presence of esters or keton ...[more]

PMID: 27350334

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