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Issue 22, 2009
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Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles

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Abstract

We report geometry-dependent cyclizations of o-alkynylaryl ketoximes and nitrones catalyzed by gold complexes. (E)-Ketoximes undergo N-attack to give isoquinoline-N-oxides. In sharp contrast, (Z)-ketoximes undergo unprecedented O-nucleophilic attack, followed by a redox cascade leading to a novel catalytic entry to isoindoles of diverse scope. The structure of an isoindole was unambiguously supported by X-ray crystallography. We demonstrated the generality of the isoindole synthesis from either (Z)-oximes or nitrones, and presented a mechanistic model of this redox cascade based on the reaction profiles of various substrates.

Graphical abstract: Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles

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Publication details

The article was received on 02 Jun 2009, accepted on 23 Jul 2009 and first published on 01 Sep 2009


Article type: Paper
DOI: 10.1039/B910757F
Citation: Org. Biomol. Chem., 2009,7, 4744-4752

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    Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles

    H. Yeom, Y. Lee, J. Lee and S. Shin, Org. Biomol. Chem., 2009, 7, 4744
    DOI: 10.1039/B910757F

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