4.7 Article

N-Heterocyclic Carbene-Catalyzed Umpolung Formal [3+3] Cycloaddition of Enals with Isatogens: Access to Fused Indolin-3-ones with a Tetrasubstituted Carbon Stereocenter

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 5, Pages 923-927

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201401070

Keywords

carbenes; cycloaddition; fused indolin-3-ones; organocatalysis; umpolung reaction

Funding

  1. National Natural Science Foundation of China [21002124, 81172933]
  2. Jiangsu Provincial Natural Science Foundation of China [BK20131305]
  3. Fundamental Research Funds for the Central Universities [JKZD2013002]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions

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A novel synthetic method to access fused indolin-3-ones with a tetrasubstituted carbon stereocenter has been developed via NHC-catalyzed umpolung formal [3+3] cycloaddtion of enals with isatogens. This methodology could be also applied for the quick construction of the 6-5-5 tricyclic pyrrolo[1,2-a]indole skeleton which is frequently found as a core structure of many indole alkaloids.

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