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Zirconocene-promoted synthesis of substituted tetrahydropyrans

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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.

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Acknowledgments

This work was supported by the University of Tennessee at Chattanooga Grote Chemistry Fund.

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Authors and Affiliations

  1. Department of Chemistry, The University of Tennessee at Chattanooga, 615 McCallie Ave., Chattanooga, TN, 37403, USA

    Bradley A. McKeown, Shanelle L. Newton & Kyle S. Knight

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  1. Bradley A. McKeown
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  2. Shanelle L. Newton
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  3. Kyle S. Knight
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Correspondence to Kyle S. Knight.

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McKeown, B.A., Newton, S.L. & Knight, K.S. Zirconocene-promoted synthesis of substituted tetrahydropyrans. Transition Met Chem 38, 129–131 (2013). https://doi.org/10.1007/s11243-012-9669-1

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  • DOI: https://doi.org/10.1007/s11243-012-9669-1

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