190730-19-9Relevant academic research and scientific papers
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.
Diastereoselective synthesis of α,α'-disubstituted oxygen heterocycles
Craig, Donald C.,Edwards, Gavin L.,Muldoon, Craig A.
, p. 6171 - 6182 (2007/10/03)
Treatment of the para -toluenesulfonyl iodide adducts of a series of I-substituted 5-hexenols with K[N(TMS)2]] gave 2,6-disubstituted tetrahydropyrans with excellent cis-diastereoselectivity. The corresponding pentenols gave the 2,5-disubstituted tetrahydrofurans as 1:1 cis:trans mixtures.
