Synthesis of 2,3-trans disubstituted tetrahydrofurans through sequential xanthate radical addition-substitution reactions

An alternate strategy is presented, to prepare 2,3-disubstituted tetrahydrofurans based on the group transfer reactions of S-alkyl dithiocarbonates (xanthates) followed by their substitution. From 2,3-dihydrofuran derivatives, the displacement of the resulting anomeric xanthates with various nucleophiles in the presence of Lewis acid allowed the formation of new carbon-carbon and carbon-heteroatom bonds.