Journal
ORGANIC LETTERS
Volume 17, Issue 21, Pages 5408-5411Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02755
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Funding
- INSA Rouen
- Rouen University
- CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- 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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