Unusual Formal [1+4] Annulation through Tandem P(NMe2)3‐Mediated Cyclopropanation/Base‐Catalyzed Cyclopropane Rearrangement: Facile Syntheses of Cyclopentenimines and Cyclopentenones |
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| Authors: | Dr Rong Zhou Kai Zhang Ling Han Yusong Chen Prof?Dr Ruifeng Li Prof?Dr Zhengjie He |
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| Institution: | 1. College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan, P. R. China;2. The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, P. R. China |
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| Abstract: | An unusual formal 1+4] annulation of α‐dicarbonyl compounds with 1,1‐dicyano‐1,3‐dienes has been realized, leading to facile syntheses of cyclopentenimines and cyclopentenones in a unique manner. Mechanistic investigation implies that this reaction takes place through a P(NMe2)3‐mediated cyclopropanation followed by a base‐catalyzed cyclopropane rearrangement. It therefore represents an unprecedented 1+4] annulation mode involving Kukhtin–Ramirez adducts. |
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| Keywords: | annulation dipoles cyclopentenes cyclopropanation rearrangement |
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