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Gold-catalyzed N,O-functionalization of 1,4-diyn-3-ols with N-hydroxyanilines to form highly functionalized pyrrole derivatives

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Abstract

This work describes new N,O-functionalization of 1,4-diyn-3-ols with N-hydroxyanilines to yield highly functionalized pyrrole derivatives. In a postulated mechanism, N-hydroxyaniline attacks the more electron-rich alkynes via regioselective N-attack to form unstable ketone-derived nitrones that react with their tethered alkynes via an intramolecular oxygen-transfer to form α-oxo gold carbenes. This new method is applicable to a short synthesis of a bioactive molecule, a PDE4 inhibitor.

Graphical abstract: Gold-catalyzed N,O-functionalization of 1,4-diyn-3-ols with N-hydroxyanilines to form highly functionalized pyrrole derivatives

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Publication details

The article was received on 15 Jan 2018, accepted on 01 Feb 2018 and first published on 01 Feb 2018


Article type: Communication
DOI: 10.1039/C8CC00330K
Citation: Chem. Commun., 2018, Advance Article
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    Gold-catalyzed N,O-functionalization of 1,4-diyn-3-ols with N-hydroxyanilines to form highly functionalized pyrrole derivatives

    Y. Hsu, S. Hsieh, P. Li and R. Liu, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC00330K

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