200641-07-2Relevant articles and documents
A Stereoselective Approach to 2,6-Disubstituted Tetrahydropyrans by Conjugate Addition Reactions of Vinyl Sulfones
Craig,Edwards,Muldoon
, p. 1318 - 1320 (2007/10/03)
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.