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Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones

Abstract : An unprecedented multicomponent organocatalyzed Knoevenagel–aza-Michael–cyclocondensation reaction between Meldrum’s acid, hydroxylamines, and aldehydes afforded a straightforward entry to a large array of racemic and syn-diastereoenriched isoxazolidinones as synthetically useful scaffolds. This process revealed a markedly facile aza-Michael–cyclocondensation sequence as a key domino reaction between RCO2NHOH and transient alkylidene Meldrum’s acid upon Brønsted base catalysis.
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Submitted on : Friday, February 22, 2019 - 3:31:58 PM
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Christophe Berini, Muriel Sebban, Hassan Oulyadi, Morgane Sanselme, Vincent Levacher, et al.. Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Organic Letters, American Chemical Society, 2015, 17 (21), pp.5408-5411. ⟨10.1021/acs.orglett.5b02755⟩. ⟨hal-02046141⟩



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