Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles
Carlos R. Gonçalves, Miran Lemmerer, Christopher J. Teskey, Pauline Adler, Daniel Kaiser, Boris Maryasin, Leticia González and Nuno Maulide*
*Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria,
Email: nuno.maulide
univie.ac.at
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.
DOI: 10.1021/jacs.9b06956
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Abstract
By rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides.
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see article for more examples
Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides
A. de la Torre, D. Kaiser, N. Maulide, J. Am. Chem. Soc., 2017, 139, 6578-6581.
Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides
V. Tona, A. de la Torre, M. Padmanaban, S. Ruider, L. González, N. Maulide, J. Am. Chem. Soc., 2016, 138, 8348-8351.
Key Words
α-chlorination, α-bromination, α-iodination, α-hydroxylation, α-amination, sulfonamides, sulfides, pyridine N-oxides
ID: J48-Y2019
