Synthesis and Application of β-Substituted Pauson–Khand Adducts: Trifluoromethyl as a Removable Steering Group

Authors

  • Nuria Aiguabella,

    1. Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10, 08028 Barcelona (Spain)
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  • Dr. Carlos del Pozo,

    1. Dept. de Química Orgánica, Universidad de Valencia, 46100 Burjassot (Spain)
    2. Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia (Spain)
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  • Prof. Xavier Verdaguer,

    1. Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10, 08028 Barcelona (Spain)
    2. Dept. de Química Orgànica, Universitat de Barcelona, Martí i Franqués, 1, 08028 Barcelona (Spain)
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  • Prof. Santos Fustero,

    1. Dept. de Química Orgánica, Universidad de Valencia, 46100 Burjassot (Spain)
    2. Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia (Spain)
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  • Prof. Antoni Riera

    Corresponding author
    1. Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10, 08028 Barcelona (Spain)
    2. Dept. de Química Orgànica, Universitat de Barcelona, Martí i Franqués, 1, 08028 Barcelona (Spain)
    • Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10, 08028 Barcelona (Spain)
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  • We thank the Spanish Ministerio de Economia y Competitividad (CTQ2011-23620), the Generalitat de Catalunya (2009SGR 00901), and IRB Barcelona for financial support. N.A. thanks the MICINN for a fellowship.

Abstract

original image

Against the rules: The synthesis of the previously unknown β-substituted regioisomers of the intermolecular Pauson–Khand reaction of terminal alkynes is reported. This regiochemistry was achieved by using the trifluoromethyl group as a removable directing group on the alkyne.

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