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Phosphine-Catalyzed Annulations of 4,4-Dicyano-2-Methylenebut-3-enoates with Maleimides and Maleic Anhydride
Alternative Title膦催化的贫电子共轭二烯和马来酰亚胺和马来酸酐的环化反应
Zhang XN(张肖楠); Chen GQ(陈根强); Tang XY(唐翔鹰); Wei Y(魏音); Shi M(施敏)
2014
Source PublicationAngew. Chem.-Int. Edit.
Volume53Issue:40Pages:10768-10773
AbstractA novel phosphine-catalyzed [4+1] annulation of maleimides with 4,4-dicyano-2-methylenebut-3-enoates has been developed to afford spirocyclic products, and the maleimides serves as C-1 synthons. Moreover, a phosphinecatalyzed formal [3+2] annulation between 4,4-dicyano-2-methylenebut-3-enoates and maleic anhydride has been also achieved, and maleic anhydride behaved as a C-3 synthon in the reaction, thus efficiently affording the functionalized cyclopentenones. A stable phosphinium-containing zwitterionic compound is the key reactive intermediate in both annulations and was successfully isolated. Plausible mechanisms have been proposed on the basis of control experiments and deuterium-labeling experiments.
Subject Area金属有机化学
DOI10.1002/anie.201406100
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Indexed BySCI
Language英语
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39112
Collection金属有机化学国家重点实验室
Corresponding AuthorShi M(施敏)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
Zhang XN,Chen GQ,Tang XY,et al. Phosphine-Catalyzed Annulations of 4,4-Dicyano-2-Methylenebut-3-enoates with Maleimides and Maleic Anhydride[J]. Angew. Chem.-Int. Edit.,2014,53(40):10768-10773.
APA 张肖楠,陈根强,唐翔鹰,魏音,&施敏.(2014).Phosphine-Catalyzed Annulations of 4,4-Dicyano-2-Methylenebut-3-enoates with Maleimides and Maleic Anhydride.Angew. Chem.-Int. Edit.,53(40),10768-10773.
MLA 张肖楠,et al."Phosphine-Catalyzed Annulations of 4,4-Dicyano-2-Methylenebut-3-enoates with Maleimides and Maleic Anhydride".Angew. Chem.-Int. Edit. 53.40(2014):10768-10773.
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