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Formal [5+3] Cycloaddition between Isatin-Based α-(Trifluoromethyl)imine Ylides and Vinyloxiranes: Diastereoselective Access to Medium-Heterocycle-Fused Spirooxindoles
Synlett ( IF 2 ) Pub Date : 2020-10-22 , DOI: 10.1055/s-0040-1706537
Hong-Wu Zhao 1 , Li-Ru Wang 1 , Wan-Qiu Ding 1 , Jia-Ming Guo 1 , Zhe Tang 1 , Xiu-Qing Song , Hui-Hui Wu 1 , Xiao-Zu Fan 1 , Xiao-Fan Bi 1 , Qi-Di Zhong 2
Affiliation  

In the presence of Pd2(dba)3·CHCl3 (2.5 mol%), PPh3 (10 mol%), and 60% NaH (1.5 equiv), the formal [5+3] cycloaddition between isatin-based α-(trifluoromethyl)imines and vinyloxiranes proceeded readily in 1,2-DCE at 40 ℃ and afforded cis-configured medium-heterocycle-fused spirooxindoles in the reasonable chemical yields with >20:1 dr. The relative stereochemical configuration of the title products was identified by X-ray diffraction analysis.

中文翻译:

基于靛红的 α-(三氟甲基)亚胺叶立德和乙烯基环氧乙烷之间的正式 [5+3] 环加成反应:非对映选择性获得中等杂环稠合螺环吲哚

在 Pd2(dba)3·CHCl3 (2.5 mol%)、PPh3 (10 mol%) 和 60% NaH (1.5 当量) 存在下,基于靛红的 α-(三氟甲基) 之间的正式 [5+3] 环加成反应亚胺和乙烯基环氧乙烷在 40 ℃下在 1,2-DCE 中容易进行,并以合理的化学产率提供顺式构型的中等杂环稠合螺吲哚,> 20:1 dr。标题产物的相对立体化学构型通过 X 射线衍射分析确定。
更新日期:2020-10-22
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