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Synlett 1997; 1997(11): 1318-1320
DOI: 10.1055/s-1997-1016
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A Stereoselective Approach to 2,6-Disubstituted Tetrahydropyrans by Conjugate Addition Reactions of Vinyl Sulfones

D. C. Craig, G. L. Edwards* , C. A. Muldoon
  • *School of Chemistry, University of New South Wales, N.S.W., 2052, Australia, FAX: (+) 61 2 9385 6141, E-mail: g.edwards@unsw.edu.au
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Publication History

Publication Date:
31 December 2000 (online)

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A highly stereoselective synthesis of cis-2,6-disubstituted tetrahydropyrans from functionalised 5-hexen-1-ols has been developed. Free radical addition of para-toluenesulfonyl iodide to the hexenol and DBU-mediated elimination of HI from the intermediate β-iodosulfones gives vinyl sulfones: subsequent conjugate addition of the potassium alkoxide leads to a highly stereoselective (≥30:1) cyclisation.

free radicals - sulfones - conjugate additions - tetrahydropyrans

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