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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

Supporting Info

Andrea Buzas and Fabien Gagosz*

Laboratoire de Synthse Organique, UMR 7652 CNRS/Ecole Polytechnique, 91128 Palaiseau, France

J. Am. Chem. Soc., 2006, 128 (39), pp 12614–12615

DOI: 10.1021/ja064223m

Publication Date (Web): September 12, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, gagosz@dcso.polytechnique.fr

Abstract

The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis.

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History

Published In Issue October 04, 2006
Received June 15, 2006

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Communication

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