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.
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.
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DOI：
10.1021/acs.joc.8b01245
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发表时间：
2018-06
期刊：
影响因子：
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通讯作者：
Yong-Xing Song;D. Du
中科院分区：
文献类型：
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作者：
Yong-Xing Song;D. Du
在方酰胺催化下，罗丹宁衍生物与N-（2，2，2-三氟乙基）靛红酮亚胺发生不对称多米诺Michael/Mannich [3 + 2]环加成反应，合成了多种双螺[羟吲哚-吡咯烷-罗丹宁]，产率高达99%，立体选择性高达99% ee和99：1 dr.将具有生物活性的若丹宁、羟吲哚和吡咯烷部分嵌入到这些新的双螺环化合物中，这将为丰富具有潜在医学价值的手性杂环化合物数据库提供一定的支持。
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.