One‐Pot Stereoselective Synthesis of 2‐Acylaziridines and 2‐Acylpyrrolidines from N‐(Propargylic)hydroxylamines |
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Authors: | Yoshiaki Miyamoto Norihiro Wada Dr Takahiro Soeta Dr Shuhei Fujinami Prof?Dr Katsuhiko Inomata Prof?Dr Yutaka Ukaji |
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Institution: | Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920‐1192 (Japan), Fax: (+81)?76‐264‐5742 |
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Abstract: | The stereoselective direct transformation of N‐(propargylic)hydroxylamines into cis‐2‐acylaziridines was achieved by the combined use of AgBF4 and CuCl. Copper salts were found to promote the transformation of the intermediary 4‐isoxazolines into 2‐acylaziridines and both 3‐aryl‐ and 3‐alkyl‐substituted 2‐acylaziridines could be prepared by using this method. Furthermore, subsequent 1,3‐dipolar cycloaddition of azomethine ylides that were generated in situ from the intermediary 2‐acylaziridines with maleimides was achieved in a stereoselective one‐pot procedure to afford the corresponding 2‐acylpyrrolidines, which consisted of an octahydropyrrolo3,4‐c]pyrrole skeleton. |
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Keywords: | 2‐acylaziridine azomethine ylides cycloaddition heterocycles rearrangement |
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