Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 7, Issue 22, Pages 4744-4752Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b910757f
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Funding
- Korean Research Foundation [KRF-2008-314-C00213]
- Korea Science and Engineering Foundation [R01-2006-11283]
- BK21 program
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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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