CHIRAL OXETANES FROM SUGAR LACTONES: SYNTHESIS OF DERIVATIVES OF 3,5-ANHYDRO-1,2-O-ISOPROPYLIDENE-α-D-GLUCURONIC ACID AND OF 3,5-ANHYDRO-1,2-O-ISOPROPYLIDENE-β-L-IDURONIC ACID

Article abstract of DOI:10.1016/S0040-4039(00)96614-0

Ring contraction reactions of triflates of α-hydroxy-γ-lactones provide an approach to the sythesis of chiral polyfunctionalised oxetanes from sugars.Treatment of 1,2-O-isopropylidene-5-O-trifluoromethanesulphonyl-α-D-glucuronolactone with benzylamine or with potassium carbonate in methanol gave ring contraction reactions to form oxetanes in good yield.