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Beilstein J Org Chem. 2011;7:802-7. doi: 10.3762/bjoc.7.91. Epub 2011 Jun 14.

A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers.

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1
Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, U.S.A.

Abstract

The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPure(TM) MPA is an efficient scavenging reagent that halts the reaction progress.

KEYWORDS:

Au-catalyzed; SN2'; allylic alcohol; allylic ether; tetrahydropyran

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