Skeletal Rearrangement of O‐Propargylic Formaldoximes by a Gold‐Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence |
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| Authors: | Prof Dr Itaru Nakamura Shinya Gima Yu Kudo Prof Dr Masahiro Terada |
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| Institution: | 1. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, 6‐3 Aramaki Aza Aoba, Aoba‐ku, Sendai 980‐8578 (Japan);2. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan) |
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| Abstract: | Skeletal rearrangement of O‐propargylic formaldoximes, in the presence of gold catalysts, afforded 4‐methylene‐2‐isoxazolines in good to excellent yields by an intermolecular methylene transfer. In addition, the cascade reaction with maleimide in the presence of a gold catalyst afforded isoxazole derivatives by cyclization/methylene transfer and a subsequent ene reaction, whereas that using a copper catalyst gave oxazepines through a 2,3‐rearrangement. |
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| Keywords: | copper gold heterocycles rearrangements synthetic methods |
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