Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole Derivatives

An efficient stereoselective strategy for the synthesis of chiral bisspiro barbituric acid–oxindole derivatives was developed. The asymmetric Michael addition/cyclization tandem reaction between benzylidene barbituric acids and oxindolylmalonitriles was catalyzed by squaramide catalyst, and the corr...

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Published inMolecules (Basel, Switzerland) Vol. 30; no. 9; p. 2000
Main Authors Qiao, De-Jun, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 30.04.2025
MDPI
Subjects
Acids
asymmetric catalysis
barbituric acid
Biological activity
Catalysts
Drugs
Hydrocarbons
Michael addition
organocatalysis
oxindole
Solvents
Michael addition
organocatalysis
oxindole
asymmetric catalysis
barbituric acid
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Summary:An efficient stereoselective strategy for the synthesis of chiral bisspiro barbituric acid–oxindole derivatives was developed. The asymmetric Michael addition/cyclization tandem reaction between benzylidene barbituric acids and oxindolylmalonitriles was catalyzed by squaramide catalyst, and the corresponding spirocyclic products were obtained in good-to-high yields (up to 97%) with excellent stereoselectivities (up to >99% ee, >20:1 dr). At the same time, the practicality of the reaction was verified by the gram-scale preparation reaction.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules30092000