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Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights |
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| Authors: | Dr Ryu Yamasaki Dr Masato Ohashi Kyotaro Maeda Takuya Kitamura Minami Nakagawa Korehito Kato Tetsushi Fujita Ryohei Kamura Kazuto Kinoshita Dr Hyuma Masu Prof?Dr Isao Azumaya Prof?Dr Sensuke Ogoshi Prof?Dr Shinichi Saito |
| Institution: | 1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162‐8601 (Japan), Fax: (+81)?3‐5261‐4631;2. Present Address: Molecular Engineering Institute (MEI), Kinki University, 11‐6 Kayanomori, Iizuka, Fukuoka 820‐8555 (Japan);3. Graduate School of Engineering, Osaka University, Suita, Osaka 565‐0871 (Japan), Fax: (+81)?6‐6879‐7394;4. Faculty of Pharmaceutical Science at Kagawa Campus, Tokushima Bunri University, 1314‐1 Shido, Sanuki, Kagawa 769‐2193 (Japan);5. Present Address: Chemical Analysis Center, Chiba University, 1‐33 Yayoi‐cho, Inage, Chiba 263‐8522 (Japan) |
| Abstract: | A detailed study of the Ni‐catalyzed 4+3+2] cycloaddition reaction between ethyl cyclopropylideneacetate and dienynes has been conducted, resulting in the development of a new method for the synthesis of compounds containing nine‐membered rings. We studied the reactivity of various dienynes, together with their substituent and conformational effects. The mechanism of the reaction was probed by examining the stoichiometric reactions of the Ni complexes and dienynes. |
| Keywords: | cycloaddition medium‐sized rings nickel synthetic methods reaction mechanisms |