Elsevier

Tetrahedron Letters

Volume 48, Issue 14, 2 April 2007, Pages 2467-2470
Tetrahedron Letters

Lanthanide triflate catalyzed generation of N-acyliminium ions from α-amido sulfones: the synthesis of (1-alkyl-1-aryl)methyl phenyl sulfones

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Abstract

The reaction of α-amido sulfones with various aromatic and heteroaromatic compounds in the presence of a catalytic amount of lanthanide triflate provides a facile route for the synthesis of (1-alkyl-1-aryl)methyl phenyl sulfones.

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Acknowledgement

Financial support from the Center for Innovation in Chemistry: Postgraduate Education and Research Program in Chemistry (PERCH-CIC), the award of a Senior Research Scholar to V.R. and the Grant No. TRF4780020 (to P.K.) by the Thailand Research Fund are gratefully acknowledged.

References and notes (12)

  • H.E. Zaugg

    Synthesis

    (1984)
    S.M. Weinreb

    Top. Curr. Chem.

    (1997)
    Y. Kohmura et al.

    J. Org. Chem.

    (2004)
    K.J.M. Beresford

    Tetrahedron Lett.

    (2004)
    C. Spino

    Angew. Chem. Int. Ed.

    (2004)
    S.M. Weinreb et al.

    Synthesis

    (2005)
    J.A. Ellman et al.

    Acc. Chem. Res.

    (2002)
    P. Zhou et al.

    Tetrahedron

    (2004)
  • E. Marcantoni et al.

    J. Org. Chem.

    (2002)
    T. Mecozzi et al.

    Tetrahedron: Asymmetry

    (2003)
    E. Marcantoni et al.

    Tetrahedron Lett.

    (2004)
    M. Petrini et al.

    Tetrahedron Lett.

    (2005)
    M. Petrini

    Chem. Rev.

    (2005)
  • R. Ballini et al.

    Org. Lett.

    (2006)
  • S. Kobayashi et al.

    Chem. Rev.

    (1999)
    R. Bloch

    Chem. Rev.

    (1998)
    D. Enders et al.

    Tetrahedron: Asymmetry

    (1997)
    R.A. Volkmann
  • J. Takaya et al.

    Org. Lett.

    (2000)
    H.C. Aspinall et al.

    Tetrahedron Lett.

    (2002)
    A.L. Joffe et al.

    Tetrahedron Lett.

    (2004)
    T. Ollevier et al.

    J. Org. Chem.

    (2004)
  • W.N. Speckamp et al.

    Tetrahedron

    (1985)
    H. Hiemstra et al.H. De Koning et al.W.N. Speckamp et al.

    Tetrahedron

    (2000)
    B.E. Maryanoff et al.

    Chem. Rev.

    (2004)
There are more references available in the full text version of this article.

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