Stereoselective synthesis of 3-hydroxy-2-sulfonyltetrahydrofurans from β-(triethylsilyloxy)aldehydes and p-tolylsulfonyldiazomethane

A new method for the stereoselective syntheses of 2-sulfonyltetrahydrofurans from β-(triethylsilyloxy)aldehydes and p-tolylsulfonyldiazomethane in the presence of BF3·OEt2 as Lewis acid is reported. The versatility of the sulfonyl functional group allows further functionalization alpha to the sulfonyl group. For example, treatment of 2-sulfonlytetrahydrofuran 2b with BF3·OEt2 and allyl silane afforded alkylative desulfonylation product in 85% yield.