Asymmetric Construction of Bispiro[oxindole-pyrrolidine-rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of Rhodanine Derivatives with N-(2,2,2-Trifluoroethyl)isatin Ketimines

Yong Xing Song, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

65 Citations (Scopus)

Abstract

Squaramide-catalyzed asymmetric domino Michael/Mannich [3 + 2] cycloaddition reaction between rhodanine derivatives and N-(2,2,2-trifluoroethyl)isatin ketimines has been developed to synthesize various bispiro[oxindole-pyrrolidine-rhodanine]s with good to excellent yields (up to 99%) and excellent stereoselectivities (up to >99% ee and >99:1 dr). The biologically active rhodanine, oxindole, and pyrrolidine moieties were embedded in these novel bispirocyclic products, which will provide some support for the enrichment of chiral heterocyclic compound databases with potential medical value.

Original languageEnglish
Pages (from-to)9278-9290
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number16
DOIs
Publication statusPublished - 17 Aug 2018

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Song, Y. X., & Du, D. M. (2018). Asymmetric Construction of Bispiro[oxindole-pyrrolidine-rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of Rhodanine Derivatives with N-(2,2,2-Trifluoroethyl)isatin Ketimines. Journal of Organic Chemistry, 83(16), 9278-9290. https://doi.org/10.1021/acs.joc.8b01245