Download PDF
Synthesis 1995; 1995(3): 330-334
DOI: 10.1055/s-1995-3909
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >