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A Straightforward Procedure for the [2+2+2] Cycloaddition of Enediynes

Authors

  • Anaïs Geny,

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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  • Sophie Gaudrel,

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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  • Franck Slowinski,

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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  • Muriel Amatore,

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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  • Gaëlle Chouraqui,

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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  • Max Malacria,

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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  • Corinne Aubert,

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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  • Vincent Gandon

    1. Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR2769, Université Pierre et Marie Curie, Tour 44-54, 4 place Jussieu, 75252 Paris, France, Fax: (+33)-1-4427-7360
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Abstract

Enediynes undergo intramolecular [2+2+2] cycloaddition in the presence of cobalt(II) iodide (CoI2), manganese and an N-heterocyclic carbene (IPr) generated in situ from the corresponding imidazolium salt and butyllithium (BuLi). Polycyclic cyclohexadienes are obtained selectively. This new method represents an interesting alternative to those employing air-sensitive cyclopentadienylcobalt [CpCoL2 (L=CO, C2H4)] catalysts. Moreover, the N-heterocyclic carbene can be used catalytically, which is a significant improvement compared to the corresponding phosphine-based system which requires an excess of ligand.

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