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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2025-04-01
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| Series: | Molecules |
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| author | De-Jun Qiao Da-Ming Du |
| author_facet | De-Jun Qiao Da-Ming Du |
| author_sort | De-Jun Qiao |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-d8a6bfa8d7e34b8d87d6c914aee2794b |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-d8a6bfa8d7e34b8d87d6c914aee2794b2025-08-20T03:52:57ZengMDPI AGMolecules1420-30492025-04-01309200010.3390/molecules30092000Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole DerivativesDe-Jun Qiao0Da-Ming Du1Key Laboratory of Medicinal Molecule Science and Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, ChinaKey Laboratory of Medicinal Molecule Science and Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, ChinaAn 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.https://www.mdpi.com/1420-3049/30/9/2000organocatalysisasymmetric catalysisbarbituric acidoxindoleMichael addition |
| spellingShingle | De-Jun Qiao Da-Ming Du Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole Derivatives Molecules organocatalysis asymmetric catalysis barbituric acid oxindole Michael addition |
| title | Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole Derivatives |
| title_full | Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole Derivatives |
| title_fullStr | Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole Derivatives |
| title_full_unstemmed | Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole Derivatives |
| title_short | Squaramide-Catalyzed Asymmetric Michael Addition/Cyclization Reaction for the Synthesis of Chiral Bisspiro Barbituric Acid–Oxindole Derivatives |
| title_sort | squaramide catalyzed asymmetric michael addition cyclization reaction for the synthesis of chiral bisspiro barbituric acid oxindole derivatives |
| topic | organocatalysis asymmetric catalysis barbituric acid oxindole Michael addition |
| url | https://www.mdpi.com/1420-3049/30/9/2000 |
| work_keys_str_mv | AT dejunqiao squaramidecatalyzedasymmetricmichaeladditioncyclizationreactionforthesynthesisofchiralbisspirobarbituricacidoxindolederivatives AT damingdu squaramidecatalyzedasymmetricmichaeladditioncyclizationreactionforthesynthesisofchiralbisspirobarbituricacidoxindolederivatives |