Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles
- Authors
- Yeom, Hyun-Suk; Lee, Youngun; Lee, Ji-Eun; Shin, Seunghoon
- Issue Date
- Nov-2009
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC & BIOMOLECULAR CHEMISTRY, v.7, no.22, pp.4744 - 4752
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC & BIOMOLECULAR CHEMISTRY
- Volume
- 7
- Number
- 22
- Start Page
- 4744
- End Page
- 4752
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/175902
- DOI
- 10.1039/b910757f
- ISSN
- 1477-0520
- 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.
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