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.maulide
univie.ac.at
A. de la Torre, D. Kaiser, N. Maulide, J. Am. Chem. Soc., 2017, 139, 6578-6581.
DOI: 10.1021/jacs.7b02983
see article for more reactions
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.
see article for more examples
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
