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Synthesis 2012; 44(23): 3579-3589
DOI: 10.1055/s-0032-1317495
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© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)–Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization

Arun K. Ghosh*
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA   Fax: +1(765)4961612   Email: akghosh@purdue.edu
,
Jorden Kass
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA   Fax: +1(765)4961612   Email: akghosh@purdue.edu
,
Daniel R. Nicponski
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA   Fax: +1(765)4961612   Email: akghosh@purdue.edu
,
Chad Keyes
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA   Fax: +1(765)4961612   Email: akghosh@purdue.edu
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Publication History

Received: 06 July 2012

Accepted after revision: 30 September 2012

Publication Date:
06 November 2012 (online)

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Abstract

We developed a copper(II) triflate–bisphosphine complex catalyzed olefin migration and Prins cyclization which lead to the synthesis of substituted tetrahydropyran derivatives. The protocol is convenient and a variety of substituted tetrahydropyrans were obtained in good to excellent yields with excellent diastereoselectivities.

Key words

tetrahydropyrans - olefin migration - Prins cyclization - diastereoselective - metal-ligand catalyzed