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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



Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

C. R. Gonçalves, M. Lemmerer, C. J. Teskey, P. Adler, D. Kaiser, B. Maryasin, L. González, N. Maulide, J. Am. Chem. Soc., 2019, 141, 18437-18443.


Key Words

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


ID: J48-Y2017