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Leveraging Alkyne-Oximium Cyclization for the Stereoselective Synthesis of Isoxazolidine
Journal
Organic Letters
ISSN
15237060
Date Issued
2022-12-09
Author(s)
Gharpure, Santosh J.
Pal, Juhi
Pansuriya, Kaushik C.
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.