Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones.
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.
Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
Christophe
C
Berini
Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
Muriel
M
Sebban
Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
Hassan
H
Oulyadi
Normandie Univ, Laboratoire SMS- EA3233, Univ Rouen , F-76821, Mont Saint Aignan, France.
Morgane
M
Sanselme
Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
Vincent
V
Levacher
Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
Jean-François
JF
Brière