Gold(I)-Catalyzed Cyclizations of 1,6-Enynes: Alkoxycyclizations and exo/endo Skeletal Rearrangements

Authors

  • Cristina Nieto-Oberhuber,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225
    2. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
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  • M. Paz Muñoz,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
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  • Salomé López Dr.,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225
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  • Eloísa Jiménez-Núñez,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225
    2. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
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  • Cristina Nevado,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
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  • Elena Herrero-Gómez,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225
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  • Mihai Raducan,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225
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  • Antonio M. Echavarren Prof. Dr.

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225
    2. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
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Errata

This article is corrected by:

  1. Errata: Gold(I)-Catalyzed Cyclizations of 1,6-Enynes: Alkoxycyclizations and exo/endo Skeletal Rearrangements Volume 14, Issue 17, 5096, Article first published online: 29 May 2008

Abstract

Gold(I) complexes are the most active catalysts for alkoxy- or hydroxycyclization and for skeletal rearrangement reactions of 1,6-enynes. Intramolecular alkoxycyclizations also proceed efficiently in the presence of gold(I) catalysts. The first examples of the skeletal rearrangement of enynes by the endocyclic cyclization pathway are also documented. Iron(III) is also able to catalyze exo and endo skeletal rearrangements of 1,6-enynes, although the scope of this transformation is more limited. The gold(I)-catalyzed endocyclic cyclization proceeds by a mechanism different from those followed in the presence of PdII, HgII, or RhI catalysts.

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