4.8 Article

Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones

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ORGANIC LETTERS
卷 17, 期 21, 页码 5408-5411

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02755

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  1. INSA Rouen
  2. Rouen University
  3. CNRS
  4. EFRD
  5. Labex SynOrg [ANR-11-LABX-0029]
  6. region Haute-Normandie (CRUNCh network)

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An unprecedented multicomponent organocatalyzed Knoevenagel-aza-Michael cydocondensation 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 Bronsted base catalysis.

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