Leveraging Alkyne–Oximium Cyclization for the Stereoselective Synthesis of Isoxazolidine

Abstract

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.

Topics & Concepts