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

Hyun-Suk Yeom; Youngun Lee; Ji-Eun Lee; Seunghoon Shin

doi:10.1039/B910757F

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Organic & Biomolecular Chemistry

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

Hyun-Suk Yeom , Youngun Lee , Ji-Eun Lee and Seunghoon Shin

Org. Biomol. Chem., 2009, 7, 4744-4752

DOI: 10.1039/B910757F
Received 02 Jun 2009, Accepted 23 Jul 2009
First published on the web 01 Sep 2009

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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.

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Organic & Biomolecular Chemistry

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

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