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

Veronica Tona, Aurélien de la Torre, Mohan Padmanaban, Stefan Ruider, Leticia González and Nuno Maulide*

*Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria, Email: nuno.maulideunivie.ac.at

V. Tona, A. de la Torre, M. Padmanaban, S. Ruider, L. González, N. Maulide, J. Am. Chem. Soc., 2016, 138, 8348-8351.

DOI: 10.1021/jacs.6b04061 (free Supporting Information)


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Abstract

A diastereoselective α-amination of amides employing simple azides proceeds under mild conditions with release of nitrogen gas. 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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Key Words

α-amination


ID: J48-Y2016