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Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones.
Berini, Christophe; Sebban, Muriel; Oulyadi, Hassan; Sanselme, Morgane; Levacher, Vincent; Brière, Jean-François.
Affiliation
  • Berini C; Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
  • Sebban M; Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
  • Oulyadi H; Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
  • Sanselme M; Normandie Univ, Laboratoire SMS- EA3233, Univ Rouen , F-76821, Mont Saint Aignan, France.
  • Levacher V; Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
  • Brière JF; Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
Org Lett ; 17(21): 5408-11, 2015 Nov 06.
Article in En | MEDLINE | ID: mdl-26488447
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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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2015 Document type: Article Affiliation country: France Country of publication: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2015 Document type: Article Affiliation country: France Country of publication: United States