Stereoselective Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans Using an Intramolecular Allylation Strategy

Peter J. Jervis, Benson M. Kariuki and Liam R. Cox*

*School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, U.K., Email: l.r.coxbham.ac.uk

P. J. Jervis, B. M. Kariuki, L. R. Cox, Org. Lett., 2006, 8, 4637-4640.

DOI: 10.1021/ol061957v

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Abstract

A highly stereoselective route to 2,4,5-trisubstituted tetrahydropyrans employs an intramolecular allylation of a (Z)-allylsilane onto an aldehyde under Brønsted acid activation.

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Key Words

Tetrahydropyrans, Hosomi-Sakurai Reaction

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ID: J54-Y2006-3070