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Updated: Aug 19, 2025
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Leveraging Alkyne-Oximium Cyclization for the Stereoselective Synthesis of Isoxazolidine
Santosh J Gharpure1, Juhi Pal1, Kaushik C Pansuriya1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India.
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.
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