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Rhenium(VII) Catalysis of Prins Cyclization Reactions

Kwanruthai Tadpetch and Scott D. Rychnovsky*

*Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, Email: srychnovuci.edu

K. Tadpetch, S. D. Rychnovsky, Org. Lett., 2008, 10, 4839-4842.

DOI: 10.1021/ol8019204 (free Supporting Information)


Abstract

The rhenium(VII) complex O3ReOSiPh3 is a particularly effective catalyst for Prins cyclizations using aromatic and α,β-unsaturated aldehydes. The reaction conditions are mild, and the highly substituted 4-hydroxytetrahydropyran products are formed stereoselectively.

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Key Words

Prins Reaction, Tetrahydropyrans


ID: J54-Y2008-3200