5‐Hydroxy‐isoxazolidine: A New Synthetic Approach to a Privileged Heterocycle for Organic Synthesis. Issue 18 (11th May 2020)

• Record Type: Journal Article
• Authors: Presenti, Piero; Moiola, Mattia; Quadrelli, Paolo
• Is Part Of: ChemistrySelect. Volume 5:Issue 18(2020)
• Page Start: 5367
• Page End: 5373
• Publication Date: 2020-05-11
• Subjects: Allylic alcohols -- Allylsilylether -- Anti-Markovnikov addition -- Ene reactions -- Isoxazolidine -- Nitrosocarbonyl.; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202001337
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A modified pathway towards 5‐hydroxy‐isoxazolidines has been preliminarily investigated by taking advantage of the anti‐Markovnikov route in ene reactions of sterically encumbered nitrosocarbonyl intermediates in the presence of allylsilylethers. Fluoride‐mediated deprotection/cyclization of the ene adducts afforded the desired heterocycles in quantitative yields and the methodology is adaptable to a one‐pot procedure. Abstract : 5‐Hydroxy‐isoxazolidines has been preliminarily synthesized by taking advantage of the anti‐Markovnikov route in ene reactions of sterically encumbered nitrosocarbonyl intermediates in the presence of allylsilylethers. Fluoride‐mediated deprotection/cyclization of the ene adducts afforded the desired heterocycles in quantitative yields.