Communication

One-Pot Tandem Catalysis: A Concise Route to Fused Bicyclic Scaffolds from Acyclic β-Ketoesters and Alkynyl Aldehydes

  1. Dr. Lu Liu1,
  2. Lai Wei1,
  3. Dr. Yong Lu1,
  4. Prof. Dr. Junliang Zhang1,2

Article first published online: 31 AUG 2010

DOI: 10.1002/chem.201001729

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 16, Issue 39, pages 11813–11817, October 18, 2010

Additional Information

How to Cite

Liu, L., Wei, L., Lu, Y. and Zhang, J. (2010), One-Pot Tandem Catalysis: A Concise Route to Fused Bicyclic Scaffolds from Acyclic β-Ketoesters and Alkynyl Aldehydes. Chem. Eur. J., 16: 11813–11817. doi: 10.1002/chem.201001729

Author Information

  1. 1

    Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-5039

  2. 2

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (P.R. China)

Publication History

  1. Issue published online: 8 OCT 2010
  2. Article first published online: 31 AUG 2010
  3. Manuscript Received: 17 JUN 2010

Funded by

  • NSFC. Grant Number: 20702015
  • Science and Technology Commission of Shanghai Municipality
  • Ministry of Education of PRC
  • 973 program. Grant Number: 2009CB825300

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Keywords:

  • bicyclic compounds;
  • domino reactions;
  • ene reaction;
  • Nazarov cyclization;
  • one-pot reactions;
  • tandem catalysis
Thumbnail image of graphical abstract

“Quick-step” synthesis: A rapid and highly efficient route to fused polycyclic scaffolds from simple, readily available β-ketoesters and alkynyl aldehydes was developed (see scheme) as a one-pot reaction by combining three fundamental reactions, that is, the Knoevenagel condensation, Nazarov cyclization, and Conia-ene reactions. Piperidinium acetate was found to be a tandem catalyst in these one-pot reactions.

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