Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones.

Org Lett

Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.

Published: November 2015

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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http://dx.doi.org/10.1021/acs.orglett.5b02755DOI Listing

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