Synthesis of 2,4,6-trisubstituted tetrahydropyrans via 6-exo selenoetherification of unsaturated alcohols

Stereoselectivity, regioselectivity and yields in the 6-exo selenoetherification of four unsaturated diols were found to depend on the stereochemistry of the diols and on the presence of an oxygen atom close to the intermediate seleniranium ring. Silica gel was useful in order to obtain good yields. Reactions performed both under kinetic and thermodynamic control led to the same products. (C) 2001 Elsevier Science Ltd. All rights reserved.