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Synthesis 2008(20): 3356-3359  
DOI: 10.1055/s-0028-1083160
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© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Dehydrative Cyclization of Allylic Diols

Aaron Aponick*, Berenger Biannic
Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
Fax: +1(352)8460296; e-Mail: aponick@chem.ufl.edu;
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Publication History

Received 18 July 2008
Publication Date:
25 September 2008 (online)

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Abstract

The gold(I)-catalyzed cyclization of monoallylic diols is an efficient method for the formation of tetrahydropyrans from readily available, easily prepared substrates. The reaction has been shown to be general and high yielding with low catalyst loadings. Several new synthetically useful substrates and efficient methods for both their preparation and cyclization are reported.

Key words

allylic diol - dehydrative cyclization - tetrahydropyran - gold-catalysis - cross-metathesis

    References

  • 1 For leading references, see: Yeung K.-S. Paterson I. Chem. Rev.  2005,  105:  4237 
    CrossrefPubMedGoogle Scholar
  • 2 Blunt JW. Copp BR. Hu W.-P. Munro MHG. Northcote PT. Prinsep MR. Nat. Prod. Rep.  2008,  25:  35 
    CrossrefGoogle Scholar
  • 3 Aponick A. Li C.-Y. Biannic B. Org. Lett.  2008,  10:  669 
    CrossrefGoogle Scholar
  • For recent reviews on homogeneous Au-catalyzed reactions, see:
  • 4a Muzart J. Tetrahedron  2008,  64:  5815 
    Google Scholar
  • 4b Shen HC. Tetrahedron  2008,  64:  3885 
    Google Scholar
  • 4c Hashmi ASK. Chem. Rev.  2007,  107:  3180 
    Google Scholar
  • 4d Gorin DJ. Toste FD. Nature  2007,  446:  395 
    Google Scholar
  • 4e Hashmi ASK. Catal. Today  2007,  122:  211 
    Google Scholar
  • 4f Jiménez-Núñez E. Echavarren AM. Chem. Commun.  2007,  333 
    Google Scholar
  • 4g Hashmi ASK. Hutchings GJ. Angew. Chem. Int. Ed.  2006,  45:  7896 
    Google Scholar
  • 4h Hoffmann-Röder A. Krause N. Org. Biomol. Chem.  2005,  3:  387 
    Google Scholar
  • 5 Chatterjee AK. Choi T.-L. Sanders DP. Grubbs RH. J. Am. Chem. Soc.  2003,  125:  11360 
    CrossrefGoogle Scholar
  • Similar compounds have previously been prepared by cross-metathesis and from δ-valerolactone. For details, see:
  • 6a Cossy J. BouBouz S. Hoveyda AH. J. Organomet. Chem.  2001,  634:  216 
    Google Scholar
  • 6b Chen S.-H. Hong B.-C. Su C.-F. Sarshar S. Tetrahedron Lett.  2005,  46:  8899 
    Google Scholar
  • 8 For leading references on metathesis workup procedures, see: Hong SH. Grubbs RH. Org. Lett.  2007,  9:  1955 ; and references cited therein
    Google Scholar
7

We find that the most simple and effective workup method for this system involves direct adsorption of the reaction mixture onto silica gel followed immediately by column chromatography.