Generation and cycloaddition of polymer-supported azomethine ylide via a 1,2-silatropic shift of alpha-silylimines: traceless synthesis of pyrrolidine derivatives |
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| Authors: | Komatsu Mitsuo Okada Hirofumi Akaki Tatsuo Oderaotoshi Yoji Minakata Satoshi |
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| Affiliation: | Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan. komatsu@ap.chem.eng.osaka-u.ac.jp |
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| Abstract: | The 1,3-dipolar cycloaddition of polymer-supported azomethine ylides to dipolarophiles gave pyrrolidine derivatives in good yields. The azomethine ylides were generated from resin-bound alpha-silylimines via a 1,2-silatropic shift. The features of this method are not only a traceless synthesis but also a unique solid-phase route to pyrrolidines with extensive diversity. [reaction: see text] |
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