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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 17
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Original Articles

3-Halotetrahydropyran-4-one Derivatives from Homopropargyl Acetal

Jon Erik Aaseng Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway
,
Naseem Iqbal Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway
,
Jørn Eivind Tungen Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway
,
Christian A. Sperger Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway
&
Anne Fiksdahl Department of Chemistry, Norwegian University of Science and Technology, Trondheim, NorwayCorrespondence[email protected]
Pages 2458-2467 | Received 14 Jan 2014, Published online: 01 Jul 2014
 
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Abstract

A gold(I)-catalyzed regioselective method for the preparation of 3-bromo/iodo-tetrahydropyran-4-one derivatives from homopropargyl acetal is reported. A one-pot procedure based on a gold(I)-catalyzed Petasis–Ferrier rearrangement/cyclization and subsequent electrophilic halogenation was developed. Corresponding hemiacetals were not suitable substrates for the formation of the 3-halo-pyran derivatives. The present transformation is a useful method to readily afford highly substituted 3-halo-tetrahydropyran-4-ones, which are suitable substrates in a variety of reactions in further synthesis.

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