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A Meldrum's Acid Based Multicomponent Synthesis of N‐Fmoc‐isoxazolidin‐5‐ones: Entry to N‐Fmoc‐β‐amino Acids

Abstract : Newly developed conditions allowed a multicomponent KaMC reaction to take place to give previously undescribed N‐Fmoc‐isoxazolidinones. This led to a two‐step synthesis of N‐Fmoc‐β3‐amino acid analogues of the proteinogenic amino acids. A multicomponent Knoevenagel–aza‐Michael cyclocondensation (KaMC) reaction starting from Meldrum's acid has been developed with base‐sensitive N‐Fmoc‐hydroxylamine. The reaction takes place under very mild basic conditions, providing a straightforward synthetic route to various unprecedented N‐Fmoc‐isoxazolidin‐5‐ones. Subsequent chemoselective reductive cleavage of the N–O bond in the presence of Zn/AcOH allowed a short synthesis of the corresponding N‐Fmoc‐β‐amino acids.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046289
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:39:59 PM
Last modification on : Thursday, July 2, 2020 - 3:29:48 AM

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Alexandra Le Foll, Emmanuel Deau, Emilie Corrot, Laurent Bischoff, Vincent Levacher, et al.. A Meldrum's Acid Based Multicomponent Synthesis of N‐Fmoc‐isoxazolidin‐5‐ones: Entry to N‐Fmoc‐β‐amino Acids. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2017, 2017 (22), pp.3265-3273. ⟨10.1002/ejoc.201700472⟩. ⟨hal-02046289⟩

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