Elsevier

Tetrahedron Letters

Volume 42, Issue 31, 30 July 2001, Pages 5245-5247
Tetrahedron Letters

Domino metathesis of alkynyl substituted cycloolefins

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Abstract

Cycloolefins with N- and O-propargyl side chains were converted in good yields to disubstituted dihydropyrroles and dihydrofurans using Grubbs’ catalyst in a sequence of enyne metathesis, RCM–ROM and CM. Olefins employed in the final CM step were ethylene and various monosubstituted alkenes.

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Cycloolefins with N- and O-propargyl side chains were converted in good yields to dihydrofurans or dihydropyrroles using Grubbs’ catalyst in a sequence of ene-yne metathesis, RCM–ROM and CM.

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Acknowledgements

We thank the Fonds der Chemischen Industrie for financial support and Professor A. Fürstner, Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim, for compound 17c.

References (7)

  • R. Stragies et al.

    J. Am. Chem. Soc.

    (2000)
    U. Voigtmann et al.

    Synthesis

    (2000)
    H. Ovaa et al.

    Chem. Commun.

    (2000)
    R. Stragies et al.

    Tetrahedron

    (1999)
  • M. Schuster et al.

    Angew. Chem., Int. Ed. Engl.

    (1997)
    R.H. Grubbs et al.

    Tetrahedron

    (1998)
    A.J. Philips et al.

    Aldrichim. Acta

    (1999)
    A. Fürstner

    Angew. Chem., Int. Ed.

    (2000)
    S.K. Armstrong

    J. Chem. Soc., Perkin Trans. 1

    (1998)
    T.M. Trnka et al.

    Acc. Chem. Res.

    (2001)
  • R. Stragies et al.

    Angew. Chem., Int. Ed. Engl.

    (1997)
    R. Stragies et al.

    Tetrahedron Lett.

    (2000)
    M. Mori et al.

    Org. Lett.

    (2000)
There are more references available in the full text version of this article.

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