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

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...

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Bibliographic Details
Published in:Beilstein Journal of Organic Chemistry
Main Authors: Berenger Biannic, Thomas Ghebreghiorgis, Aaron Aponick
Format: Article
Language:English
Published: Beilstein-Institut 2011-06-01
Subjects:
allylic alcohol
allylic ether
Au-catalyzed
SN2'
tetrahydropyran
Online Access:https://doi.org/10.3762/bjoc.7.91
Description
Summary: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 QuadraPureTM MPA is an efficient scavenging reagent that halts the reaction progress.
ISSN:1860-5397

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