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Synthesis 1995; 1995(3): 330-334
DOI: 10.1055/s-1995-3909
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Metal Mediated One-Pot Synthesis of Cyclopentanones from Allyl Vinyl Ethers or Diallyl Ethers via Tandem Claisen Rearrangement and Hydroacylation

Peter Eilbracht* , Alexander Gersmeier, Detlev Lennartz, Thomas Huber
  • *Organische Chemie I (FB 3), Universität Dortmund, Otto-Hahn-Str. 6, D-44221 Dortmund, Germany
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Publication Date:
31 December 2000 (online)

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Cyclopentanones 3 and 7 are generated in a one-pot procedure from allyl vinyl ethers 1 and diallyl ethers 4, respectively. The conversion is carried out in the presence of RhCl(cod)(dppe) or RuCl2(PPh3)3 at elevated temperatures and involves a sequence of aliphatic Claisen rearrangement and intramolecular hydroacylation of the pent-4-enals generated as intermediates. The diallyl ethers 4 undergo an additional double-bond isomerization prior to the Claisen rearrangement.

cyclopentanone synthesis - transition metal catalysis - hydroacylation - Claisen rearrangement - tandem procedure