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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
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-06-29 00:00:00 , DOI: 10.1021/acs.joc.8b01245
Yong-Xing Song 1 , Da-Ming Du 1
Affiliation  

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.

中文翻译:

经由方胺催化的多米诺·迈克尔/曼尼希[3 + 2]环丁胺衍生物与N-(2,2,2-三氟乙基)异丁烯酮亚胺的不对称构建Bispiro [oxindole-吡咯烷-罗丹宁] s的不对称构造。

罗丹宁衍生物与N-(2,2,2-三氟乙基)异丁烯酮酮之间的方胺催化不对称多米诺骨牌Michael / Mannich [3 + 2]环加成反应已被开发出来,可以合成出各种具有良好稳定性的双螺并[氧吲哚-吡咯烷-罗丹宁]。优异的产率(高达99%)和出色的立体选择性(高达> 99%ee和> 99:1 dr)。这些新的双螺环产物中嵌入了具有生物活性的罗丹宁,羟吲哚和吡咯烷部分,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些支持。
更新日期:2018-06-29
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