2012•SynthesisOpen access

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

Arun Kumar Ghosh, Jorden Paul Kass, Daniel R. Nicponski, Chad Keyes

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.

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Key concepts: Chemistry, Prins reaction, Tetrahydropyran, Olefin fiber, Copper, Catalysis, Trifluoromethanesulfonate, Organic chemistry