Transition Metal Chemistry

, Volume 38, Issue 2, pp 129–131 | Cite as

Zirconocene-promoted synthesis of substituted tetrahydropyrans

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


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.


  1. 1.
    Rousset CJ, Swanson DR, Lamaty F, Negishi E (1989) Tetrahedron Lett 30:5105–5108CrossRefGoogle Scholar
  2. 2.
    Negishi E (2005) Dalton Trans 5:827–848CrossRefGoogle Scholar
  3. 3.
    Uesaka N, Mori M, Okamura K, Date T (1994) J Org Chem 59:4542–4547CrossRefGoogle Scholar
  4. 4.
    Davis JM, Whitby RJ, Jaxa-Chamiec A (1994) Tetrahedron Lett 35:1445–1448CrossRefGoogle Scholar
  5. 5.
    Kemp MI, Whitby RJ, Coote SJ (1994) Synlett 6:451–453Google Scholar
  6. 6.
    Kemp MI, Whitby RJ, Coote SJ (1998) Synthesis 30:552–556Google Scholar
  7. 7.
    Owen DR, Whitby RJ (2005) Synthesis 35:2061–2074Google Scholar
  8. 8.
    Macfarlane DPS, Norton D, Whitby RJ, Tupper D (2006) Synlett 18:3439–3442Google Scholar
  9. 9.
    Hunter RA, Macfarlane DPS, Whitby RJ (2006) Synlett 18:3314–3318Google Scholar
  10. 10.
    Ito H, Nakamura T, Taguchi T, Hanzawa Y (1995) Tetrahedron 51:4507–4518CrossRefGoogle Scholar
  11. 11.
    Ito H, Ikeuchi Y, Taguchi T, Hanzawa Y, Shiro M (1994) J Am Chem Soc 116:5469–5470CrossRefGoogle Scholar
  12. 12.
    Ito H, Motoki Y, Taguchi T, Hanzawa Y (1993) J Am Chem Soc 115:8835–8836CrossRefGoogle Scholar
  13. 13.
    Knight KS, Waymouth RM (1994) Organometallics 13:2575–2577CrossRefGoogle Scholar
  14. 14.
    Ito H, Taguchi T, Hanzawa Y (1993) J Org Chem 58:774–775CrossRefGoogle Scholar
  15. 15.
    Fielding EN, Gao YS, Knight KS (2010) Transit Met Chem 35:695–698CrossRefGoogle Scholar
  16. 16.
    Milczek EL, Palmiero L, Sewell SL, Knight KS (2006) Transit Met Chem 31:27–29CrossRefGoogle Scholar
  17. 17.
    Abbott AR, Thompson J, Thompson LC, Knight KS (2003) Transit Met Chem 28:305–307CrossRefGoogle Scholar
  18. 18.
    Beihoffer LA, Craven RA, Knight KS, Sisson CR, Waddell TG (2005) Transit Met Chem 30:582–585CrossRefGoogle Scholar

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

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