Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages 802-807Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.91
Keywords
allylic alcohol; allylic ether; Au-catalyzed; S(N)2 '; tetrahydropyran
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Funding
- Florida Department of Health [09-KN-01-23124]
- Petra Research, Inc.
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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.
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