(Polyfluoro)silane-mediated generation of azomethine ylides from imines and their cycloaddition leading to N-heterocycles |
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Authors: | Mitsuo Komatsu Hirofumi OkadaSeiji Yokoi Satoshi Minakata |
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Institution: | Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan |
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Abstract: | The novel generation and cycloaddition of azomethine ylides from an α-(trimethylsilyl)imine using (polyfluoro)silanes is described. The method was successfully applied to an efficient one-pot process. Namely, an azaallyl anion, generated by abstraction of the hydrogen α to an imino nitrogen, was treated with a di- or trifluorosilane to give an azomethine ylide intermediate below room temperature. The generated 1,3-dipole was smoothly trapped with dipolarophiles to afford nitrogen-containing five-membered heterocycles in good yields. |
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Keywords: | azomethine ylide 1 3-dipolar cycloaddition fluorosilane α-silylimine pyrrolidine |
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