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

Molecules

Key Laboratory of Medicinal Molecule Science and Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China.

Published: April 2025


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Article Abstract

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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12073245PMC
http://dx.doi.org/10.3390/molecules30092000DOI Listing

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