Oxidation-Initiated Cyclizations of Pentadienyl Ethers: An Alternative Entry to the Nazarov Reaction.

Angew Chem Int Ed Engl

Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2, Canada.

Published: May 2017

AI Article Synopsis

  • The study focuses on oxidation-initiated Nazarov reactions involving 1,4-pentadien-3-yl ethers in the presence of DDQ, a well-known oxidizing agent.
  • These reactions lead to the formation of cyclopentanone products that maintain both newly created stereocenters and an exocyclic methylene unit by means of regioselective elimination.
  • Additionally, the research introduces a method utilizing catalytic DDQ paired with MnO as the final oxidant to enhance the reaction process.

Article Abstract

Oxidation-initiated Nazarov reactions of 1,4-pentadien-3-yl ethers take place in the presence of DDQ. Termination by regioselective elimination preserves both stereocenters created during electrocyclization, providing cyclopentanone products bearing an exocyclic methylene unit. Use of catalytic DDQ with MnO as terminal oxidant is also described.

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Source
http://dx.doi.org/10.1002/anie.201701748DOI Listing

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