Full Paper

Ni-Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights

  1. Dr. Ryu Yamasaki1,2,
  2. Dr. Masato Ohashi3,
  3. Kyotaro Maeda1,
  4. Takuya Kitamura1,
  5. Minami Nakagawa1,
  6. Korehito Kato1,
  7. Tetsushi Fujita1,
  8. Ryohei Kamura3,
  9. Kazuto Kinoshita3,
  10. Dr. Hyuma Masu4,5,
  11. Prof. Dr. Isao Azumaya4,
  12. Prof. Dr. Sensuke Ogoshi3,*,
  13. Prof. Dr. Shinichi Saito1,*

Article first published online: 25 JAN 2013

DOI: 10.1002/chem.201204087

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 19, Issue 10, pages 3415–3425, March 4, 2013

Additional Information

How to Cite

Yamasaki, R., Ohashi, M., Maeda, K., Kitamura, T., Nakagawa, M., Kato, K., Fujita, T., Kamura, R., Kinoshita, K., Masu, H., Azumaya, I., Ogoshi, S. and Saito, S. (2013), Ni-Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights. Chem. Eur. J., 19: 3415–3425. doi: 10.1002/chem.201204087

Author Information

  1. 1

    Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631

  2. 2

    Present Address: Molecular Engineering Institute (MEI), Kinki University, 11-6 Kayanomori, Iizuka, Fukuoka 820-8555 (Japan)

  3. 3

    Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394

  4. 4

    Faculty of Pharmaceutical Science at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193 (Japan)

  5. 5

    Present Address: Chemical Analysis Center, Chiba University, 1-33 Yayoi-cho, Inage, Chiba 263-8522 (Japan)

*Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394

Publication History

  1. Issue published online: 22 FEB 2013
  2. Article first published online: 25 JAN 2013
  3. Manuscript Received: 15 NOV 2012

Funded by

  • Society of Synthetic Organic Chemistry of Japan

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Keywords:

  • cycloaddition;
  • medium-sized rings;
  • nickel;
  • synthetic methods;
  • reaction mechanisms

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.

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