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.
Org. Lett., 2006, 8 (20), pp 4649–4652
DOI: 10.1021/ol061957v
Publication Date (Web): September 2, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, l.r.cox@bham.ac.uk

Abstract

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A highly stereoselective route to 2,4,5-trisubstituted tetrahydropyrans is reported. The key step employs an intramolecular allylation of a (Z)-allylsilane onto an aldehyde under Brønsted acid activation. Complete 1,4-stereoinduction accounts for the formation of only two out of the possible four THP products. The level of 1,3-stereoinduction is optimal when the reaction is carried out in an apolar solvent, which is in accord with electrostatics being key to controlling this aspect of the stereoselectivity.

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History

  • Published In Issue September 28, 2006
  • Received August 8, 2006

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