Synthesis of Nine‐Membered Carbocycles by the [4+3+2] Cycloaddition Reaction of Ethyl Cyclopropylideneacetate and Dienynes
2010; Wiley; Volume: 122; Issue: 10 Linguagem: Inglês
10.1002/ange.200907052
ISSN1521-3757
AutoresShinichi Saito, Kyotaro Maeda, Ryu Yamasaki, Takuya Kitamura, Minami Nakagawa, Korehito Kato, Isao Azumaya, Hyuma Masu,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoAngewandte ChemieVolume 122, Issue 10 p. 1874-1877 Zuschrift Synthesis of Nine-Membered Carbocycles by the [4+3+2] Cycloaddition Reaction of Ethyl Cyclopropylideneacetate and Dienynes† Shinichi Saito Prof. Dr., Shinichi Saito Prof. Dr. [email protected] Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorKyotaro Maeda, Kyotaro Maeda Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorRyu Yamasaki Dr., Ryu Yamasaki Dr. Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorTakuya Kitamura, Takuya Kitamura Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorMinami Nakagawa, Minami Nakagawa Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorKorehito Kato, Korehito Kato Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorIsao Azumaya Prof. Dr., Isao Azumaya Prof. Dr. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193 (Japan)Search for more papers by this authorHyuma Masu Dr., Hyuma Masu Dr. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193 (Japan)Search for more papers by this author Shinichi Saito Prof. Dr., Shinichi Saito Prof. Dr. [email protected] Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorKyotaro Maeda, Kyotaro Maeda Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorRyu Yamasaki Dr., Ryu Yamasaki Dr. Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorTakuya Kitamura, Takuya Kitamura Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorMinami Nakagawa, Minami Nakagawa Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorKorehito Kato, Korehito Kato Department of Chemistry, Faculty of Science, Kagurazaka, Shinjuku, Tokyo, 162-8601 (Japan), Fax: (+81) 3-5261-4631 http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorIsao Azumaya Prof. Dr., Isao Azumaya Prof. Dr. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193 (Japan)Search for more papers by this authorHyuma Masu Dr., Hyuma Masu Dr. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193 (Japan)Search for more papers by this author First published: 22 February 2010 https://doi.org/10.1002/ange.200907052Citations: 25 † Support form the Society of Synthetic Organic Chemistry (Japan) is gratefully acknowledged (Tanabe Seiyaku Award in Synthetic Organic Chemistry (Japan)). Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Effektiv reagiert eine Reihe von Dieninen mit Ethylcyclopropylidenacetat in Gegenwart von [Ni(cod)2]/PPh3 (cod=Cyclooctadien), wobei selektiv Cyclononadiene entstehen. Dienine mit aromatischen Ringsubstituenten sind ausgezeichnete Substrate, und die entsprechenden Tricyclen wurden in hoher Ausbeute erhalten. Die Reaktion eröffnet einen neuen Zugang zu neungliedrigen Carbocyclen (siehe Schema). Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description ange_200907052_sm_miscellaneous_information.pdf6.6 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46–126; 10.1002/(SICI)1521-3757(20000103)112:1 3.0.CO;2-P Google ScholarAngew. Chem. Int. Ed. 2000, 39, 44–122. 10.1002/(SICI)1521-3773(20000103)39:1 3.0.CO;2-L CASPubMedWeb of Science®Google Scholar 2For recent reviews of transition-metal-catalyzed cycloaddition reactions, see: Google Scholar 2aK. P. C. Vollhardt, Angew. 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