Transition Metal Chemistry

, Volume 38, Issue 2, pp 129–131

Zirconocene-promoted synthesis of substituted tetrahydropyrans

  • Bradley A. McKeown
  • Shanelle L. Newton
  • Kyle S. Knight
Article

DOI: 10.1007/s11243-012-9669-1

Cite this article as:
McKeown, B.A., Newton, S.L. & Knight, K.S. Transition Met Chem (2013) 38: 129. doi:10.1007/s11243-012-9669-1
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Abstract

Zirconocene reagents derived from zirconocene dichloride and two equivalents of butyllithium react with allylic, homoallylic diene ethers. Hydrolysis of the reaction products yields substituted tetrahydropyrans. The reaction is postulated to occur via cyclization of the diene to form a zirconacyclopentane. This cyclization occurs without allylic rearrangement.

Copyright information

© Springer Science+Business Media Dordrecht 2012

Authors and Affiliations

  • Bradley A. McKeown
    • 1
  • Shanelle L. Newton
    • 1
  • Kyle S. Knight
    • 1
  1. 1.Department of ChemistryThe University of Tennessee at ChattanoogaChattanoogaUSA