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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides
Veronica Tona1, Aurélien de la Torre1, Mohan Padmanaban1
1Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna , Währinger Strasse 38, 1090 Vienna, Austria.
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.
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