Leveraging Alkyne–Oximium Cyclization for the Stereoselective Synthesis of Isoxazolidine

A TMSOTf-mediated highly diastereoselective synthesis of isoxazolidine bearing three contiguous stereocenters is described. This method utilizes O-propargyl hydroxylamines as a novel building block for the rapid assembly of the isoxazolidines via alkyne-oximium cyclization. The strategy could be used in the synthesis of enantiomerically enriched isoxazolidines. Reductive cleavage of the N-O bond efficiently gives the corresponding 1,3-aminodiols with precise control over all stereocenters formed.