Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


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.

see article for more examples

see article for more reactions



Key Words

Cyclopropanols, Cyclopentenes


ID: J48-Y2006-3160