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Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes

Aurélien Blanc, Katharina Tenbrink, Jean-Marc Weibel and Patrick Pale*

*Laboratoire de Synthèse et Réactivité Organiques, associé au CNRS, Université de Strasbourg, Institut de Chimie, 4 rue Blaise Pascal, 67000 Strasbourg, France, Email: ppalechimie.u-strasbg.fr

A. Blanc, K. Tenbrink, J.-M. Weibel, P. Pale, J. Org. Chem., 2009, 74, 4360-4363.

DOI: 10.1021/jo900483m (free Supporting Information)


Abstract

A convenient, silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol gives functionalized furans. Evidence supported a cascade mechanism.

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proposed mechanism



Key Words

Furans


ID: J42-Y2009-1640