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Cycloisomerization of 1,n-Enynes: Challenging Metal-Catalyzed Rearrangements and Mechanistic Insights

Authors

  • Véronique Michelet Dr.,

    1. Laboratoire de Synthèse Sélective Organique et Produits Naturels, UMR 7573, Ecole Nationale Supérieure de Chimie de Paris, 11, rue P. et M. Curie, 75231 Paris cedex 05, France, Fax: (+33) 1-4407-1062
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  • Patrick Y. Toullec Dr.,

    1. Laboratoire de Synthèse Sélective Organique et Produits Naturels, UMR 7573, Ecole Nationale Supérieure de Chimie de Paris, 11, rue P. et M. Curie, 75231 Paris cedex 05, France, Fax: (+33) 1-4407-1062
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  • Jean-Pierre Genêt Prof.

    1. Laboratoire de Synthèse Sélective Organique et Produits Naturels, UMR 7573, Ecole Nationale Supérieure de Chimie de Paris, 11, rue P. et M. Curie, 75231 Paris cedex 05, France, Fax: (+33) 1-4407-1062
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Abstract

Metal-catalyzed cycloisomerization reactions of 1,n-enynes have appeared as conceptually and chemically highly attractive processes as they contribute to the highly demanded search for atom economy and allow the discovery of new reactions. Since the pioneering studies with palladium by the research group of Barry Trost in the mid-1980s, several other metals have been identified as excellent catalysts for the rearrangement of enyne skeletons. Moreover, the behavior of 1,n-enynes may be influenced by other functional groups such as alcohols, aldehydes, ethers, alkenes, or alkynes, thus enhancing the molecular complexity of the synthesized products. Apart from the intrinsic rearrangements of 1,n-enynes, several tandem reactions incorporating intramolecular trapping agents or intermolecular partners have been discovered. This Review aims to highlight the main contributions in this field of catalysis and to propose and comment on the mechanistic insights of the recent discoveries.

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