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Berini C, Sebban M, Oulyadi H, et al. Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Org Lett. 2015;17(21):5408-11doi: 10.1021/acs.orglett.5b02755.
Berini, C., Sebban, M., Oulyadi, H., Sanselme, M., Levacher, V., & Brière, J. F. (2015). Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Organic letters, 17(21), 5408-11. https://doi.org/10.1021/acs.orglett.5b02755
Berini, Christophe, et al. "Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones." Organic letters vol. 17,21 (2015): 5408-11. doi: https://doi.org/10.1021/acs.orglett.5b02755
Berini C, Sebban M, Oulyadi H, Sanselme M, Levacher V, Brière JF. Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Org Lett. 2015 Nov 06;17(21):5408-11. doi: 10.1021/acs.orglett.5b02755. Epub 2015 Oct 21. PMID: 26488447.
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Org Lett. 2015 Nov 06;17(21):5408-11. doi: 10.1021/acs.orglett.5b02755. Epub 2015 Oct 21.

Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones.

Organic letters

Christophe Berini, Muriel Sebban, Hassan Oulyadi, Morgane Sanselme, Vincent Levacher, Jean-François Brière

Affiliations

  1. Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.
  2. Normandie Univ, Laboratoire SMS- EA3233, Univ Rouen , F-76821, Mont Saint Aignan, France.

PMID: 26488447 DOI: 10.1021/acs.orglett.5b02755

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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