A Tandem Olefin Migration and Prins Cyclization Using Cu(OTf)(2)-Bisphosphine Complexes: An Improved Synthesis of Functionalized Tetrahydropyrans.

Tetrahedron Lett

Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.

Published: July 2012

In situ-generated (bis-DPPMB)-Cu(OTf)(2) complex has been examined to catalyze a tandem olefin migration and Prins cyclization of an alkenol with various aldehydes. The reaction proceeded with electron-rich aromatic aldehydes at room temperature and provided functionalized tetrahydropyrans in good yields. An efficient synthesis of the bis-DPPMB ligand has also been described.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3383828PMC
http://dx.doi.org/10.1016/j.tetlet.2012.04.006DOI Listing

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