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]

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.

GRAPHICAL ABSTRACT

Keywords:

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

3-Halotetrahydropyran-4-one Derivatives from Homopropargyl Acetal

Information for

Open access

Opportunities

Help and information

3-Halotetrahydropyran-4-one Derivatives from Homopropargyl Acetal

Abstract

GRAPHICAL ABSTRACT

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature