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. 2015 Nov 6;17(21):5408-11.
doi: 10.1021/acs.orglett.5b02755. Epub 2015 Oct 21.

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
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Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones

Christophe Berini et al. Org Lett. .

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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