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PtII-Catalyzed Synthesis of 9-Oxabicyclo[3.3.1]nona-2,6-dienes from 2-Alkynyl-1-carbonylbenzenes and Allylsilanes by an Allylation/Annulation Cascade†

  1. Sabyasachi Bhunia,
  2. Kuo-Chang Wang,
  3. Rai-Shung Liu Prof. Dr.

Article first published online: 28 MAY 2008

DOI: 10.1002/anie.200800826

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 27, pages 5063–5066, June 23, 2008

Additional Information

How to Cite

Bhunia, S., Wang, K.-C. and Liu, R.-S. (2008), PtII-Catalyzed Synthesis of 9-Oxabicyclo[3.3.1]nona-2,6-dienes from 2-Alkynyl-1-carbonylbenzenes and Allylsilanes by an Allylation/Annulation Cascade. Angew. Chem. Int. Ed., 47: 5063–5066. doi: 10.1002/anie.200800826

Author Information

  1. Department of Chemistry, National Tsing Hua University, Hsinchu 30043 (Taiwan), Fax: (+886) 3571-1082

  1. †

    We thank the National Science Council, Taiwan for support of this work.

Publication History

  1. Issue published online: 16 JUN 2008
  2. Article first published online: 28 MAY 2008
  3. Manuscript Received: 20 FEB 2008

Funded by

  • National Science Council, Taiwan

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Keywords:

  • allylation;
  • annulation;
  • oxygen heterocycles;
  • platinum
Thumbnail image of graphical abstract

Platinum is key: A new catalytic synthesis of 9-oxabicyclo[3.3.1]nona-2,6-dienes from readily available 2-alkynyl-1-carbonylbenzenes, allylsilanes, and water is reported (see scheme). This reaction sequence is proposed to proceed through a series of three reactions, including allylation of the carbonyl group, hydroalkoxylation of the alkyne, and a new ene-oxonium annulation.

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