Room Temperature Au(I)-Catalyzed exo-Selective Cycloisomerization of Acetylenic Acids: An Entry to Functionalized γ-Lactones

Emilie Genin, Patrick Yves Toullec, Sylvain Antoniotti, Célia Brancour, Jean-Pierre Genêt* and Véronique Michelet*

*Laboratoire de Synthèse Sélective Organique et Produits Naturels, E.N.S.C.P., UMR 7573, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France, Email: jean-pierre-genetenscp.fr, veronique-micheletenscp.fr

E. Genin, P. Y. Toullec, S. Antioniotti, C. Brancour, J.-P. Genêt, V. Michelet, J. Am. Chem. Soc., 2006, 128, 3112-3113.

DOI: 10.1021/ja056857j (free Supporting Information)

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Abstract

A highly efficient gold-catalyzed cyclization reaction of various functionalized acetylenic leads to γ-lactones in good to excellent yields. The reaction conditions are compatible with several functional groups, such as ester, alkene, alkyne, chloro, and free or protected alcohol.

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Au₂O₃ as a Stable and Efficient Catalyst for the Selective Cycloisomerization of γ-Acetylenic Carboxylic Acids to γ-Alkylidene-γ-Butyrolactones

P. Y. Toullec, E. Genin, S. Antoniotti, J.-P. Genêt, V. Michelet, Synlett, 2008, 707-711.

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Key Words

Lactones

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ID: J48-Y2006-1650