Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction of unsaturated imines |
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| Authors: | Katsunori Tanaka Eric RO SiwuShinji Hirosaki Takayuki IwataRisa Matsumoto Yasutaka KitagawaAmbara R Pradipta Mitsutaka OkumuraKoichi Fukase |
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| Institution: | a Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
b RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan |
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| Abstract: | Formal 4+4] reaction of the unsaturated benzyl- or allylimines, which is efficiently mediated by primary amine, provides the 2,6,9-triazabicyclo3.3.1]nonane derivatives. Variously substituted homo- and hetero-coupling products are obtained in good to excellent yields by quite a simple procedure under mild conditions: by mixing the unsaturated aldehydes with the amines at room temperature. |
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| Keywords: | Formal [4+4] reaction 2 6 9-Triazabicyclo[3 3 1]nonane Benzylamine Unsaturated imine Aminoacetal |
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