Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones

Christophe Berini (1) , Muriel Sebban (1) , Hassan Oulyadi (1) , Morgane Sanselme (2) , Vincent Levacher (1) , Jean-François Brière (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 SMS - Sciences et Méthodes Séparatives

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.

Domains: Chemical Sciences

Christophe Berini, Muriel Sebban, Hassan Oulyadi, Morgane Sanselme, Vincent Levacher, et al.. Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Organic Letters, 2015, 17 (21), pp.5408-5411. ⟨10.1021/acs.orglett.5b02755⟩. ⟨hal-02046141⟩