Trimethylsilyl trifluoromethanesulfonate-catalyzed reaction of 2-((trimethylsilyl)oxy)furan with nitrones

Trimethylsilyl trifluoromethanesulfonate catalyzes the reaction of nitrones with 2-((trimethylsilyl)oxy)furan, producing bicyclic isoxazolidines. Proper choice of substituents R1 and R2 of the nitrone helps achieve complementary stereochemical courses of the cycloaddition reaction. Bicyclic isoxazolidines are highly functionalized chiral building units and exhibit synthetic equivalence with stereodefined 5-amino-3,4-dihydroxyalkanoic acids.