Gold(I) Catalyzed Isomerization of 5-en-2-yn-1-yl Acetates: An Efficient Access to Acetoxy Bicyclo[3.1.0]hexenes and 2-Cycloalken-1-ones

Andrea Buzas and Fabien Gagosz*

*Laboratoire de Synthèse Organique, UMR 7652 CNRS/Ecole Polytechnique, 91128 Palaiseau, France, Email: gagoszdcso.polytechnique.fr

A. Buzas, F. Gagosz, J. Am. Chem. Soc., 2006, 128, 12614-12615.

DOI: 10.1021/ja064223m

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Abstract

A sequence of two gold(I)-catalyzed isomerization steps allows the synthesis of functionalized acetoxy bicyclo[3.1.0]hexenes from 5-en-2-yn-1-yl acetates. Acetoxy bicyclo[3.1.0]hexene products can be further transformed to 2-cycloalkenones by simple methanolysis.

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Key Words

Cyclopropanols, Cyclopentenes

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ID: J48-Y2006-3160