Ring-expansion reaction of oximes with aluminum reductants |
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| Authors: | Cho Hidetsura Iwama Yusuke Mitsuhashi Nakako Sugimoto Kenji Okano Kentaro Tokuyama Hidetoshi |
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| Institution: | Graduate School of Science, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan. hcho@mail.pharm.tohoku.ac.jp |
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| Abstract: | The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields. |
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