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

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• 作者：Veronica Tona ; Aurélien de la Torre ; Mohan Padmanaban ; Stefan Ruider ; Leticia González ; Nuno Maulide
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：July 13, 2016
• 年：2016
• 卷：138
• 期：27
• 页码：8348-8351
• 全文大小：407K
• 年卷期：0
• ISSN：1520-5126

文摘

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.