Thermally-Induced Intramolecular [4+2] Cycloaddition of Allylamino- or Allyloxy-Tethered Alkylidenecyclopropanes |
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| Authors: | Leyi Tao Dr. Yin Wei Prof. Dr. Min Shi |
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| Affiliation: | State Key Laboratory of Organometallic Chemistry, Center for Excellence Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 P. R. China |
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| Abstract: | A thermally-induced intramolecular [4+2] cycloaddition reaction of allylamino- or allyloxy-tethered alkylidenecyclopropanes has been reported in this paper, giving a new protocol for the rapid construction of polycyclic skeleton molecules in moderate to excellent yields with a broad substrate scope. On the basis of control experiments and DFT calculations, we disclosed that the reaction proceeded through a [4+2] cycloaddition and trace of water assisted 1,3-H shift process to give the target product. |
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| Keywords: | Alkylidenecyclopropanes [4+2] cycloaddition DFT calculations Water assistance 1,3-H shift |
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