Facile domino reactions for the stereoselective assembly of highly functionalized bis-(trans-2,3-dihydrofuranyl) sulfides

A facile stereoselective synthesis of a series of nineteen novel bis-(trans-2,3-dihydrofuranyl) sulfides from the reaction of (Z,Z)-2,2′-thiobis(1,3-diarylprop-2-en-1-ones) with substituted phenacyl bromides and pyridine in the presence of K2CO3 in acetonitrile via domino reactions is described. This transformation presumably occurs via pyridinium salt formation/ylide generation/Michael addition/intramolecular annulation domino sequence, involving the formation of two C-C and two C-O bonds and four stereocentres in a single step with complete stereoselectivity affording only one diastereomer.