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Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides

Aurélien de la Torre, Daniel Kaiser and Nuno Maulide*

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

A. de la Torre, D. Kaiser, N. Maulide, J. Am. Chem. Soc., 2017, 139, 6578-6581.

DOI: 10.1021/jacs.7b02983 (free Supporting Information)


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Abstract

Flexible and chemoselective methods for the transition-metal-free oxidation of amides provide α-keto amides and α-hydroxy amides. These highly valuable motifs are accessed in good to excellent yields and stereoselectivities with high functional group tolerance.

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One-Pot Synthesis of α-Hydroxy Amides and α-Keto Amides from the α-OTMP precursor



Key Words

α-keto amides, 2,6-lutidine-N-oxide, α-hydroxy amides, TEMPO


ID: J48-Y2017