Synlett p. 1318 - 1320 (1997)
Update date:2022-08-03
Topics:
Craig
Edwards
Muldoon
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.
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Doi:10.1021/jo01377a006
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(2020)Doi:10.1016/j.tet.2008.10.046
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(2001)Doi:10.1016/j.chemphyslip.2008.02.002
(2008)Doi:10.1039/b813870b
(2008)
