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 language | English |
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Pages (from-to) | 9278-9290 |
Number of pages | 13 |
Journal | Journal of Organic Chemistry |
Volume | 83 |
Issue number | 16 |
DOIs | |
Publication status | Published - 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