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Issue 13, 2018
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The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates

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Abstract

Catalytic C–C bond forming methods for the one-pot transformation of amides into other classes of compounds are highly demanding. In this report, we demonstrate the catalytic reductive addition of isocyanoacetates to tertiary lactams/amides to produce 5-methoxyoxazoles, including N-heterocyclic substituted oxazoles and sterically hindered amino oxazoles that are difficult to obtain by traditional oxazole-forming Ugi-type reactions. This one-pot procedure involves the Ir-catalysed partial reduction of lactams/amides and the sequential chemoselective addition of the isocyanide group in isocyanoacetates.

Graphical abstract: The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates

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Publication details

The article was received on 26 Mar 2018, accepted on 16 May 2018 and first published on 17 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00312B
Citation: Org. Chem. Front., 2018,5, 2051-2056
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    The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates

    X. Hu, T. Shen, D. Cai, J. Zheng and P. Huang, Org. Chem. Front., 2018, 5, 2051
    DOI: 10.1039/C8QO00312B

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