Rare C-7-substituted aziridinyl iminosugars can be synthesized through a short reaction sequence involving 1,3-cycloaddition of cyclic nitrones with alkynes and a Baldwin rearrangement of isoxazolines into bicyclic 2-acylaziridines. The method is efficient and completely diastereoselective, producing stable aziridinyl iminosugars in high yields.
A crystalline peracetylated nitrone underwent regio- and stereoselective 1,3-dipolar cycloaddition with alkynes, affording d-gluco-configured isoxazolines as a new class of iminosugars.
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