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Novel Ene-Like Cycloisomerization Reaction of Nitrile Oxides with a Tethered Allyltrimethylsilyl Group

2002; Wiley; Volume: 41; Issue: 9 Linguagem: Inglês

10.1002/1521-3773(20020503)41

1521-3773

Teruhiko Ishikawa, Jin Urano, Shushiro Ikeda, Yasuhiro Kobayashi, Seiki Saitô,

Catalytic Alkyne Reactions

Angewandte Chemie International EditionVolume 41, Issue 9 p. 1586-1588 Communication Novel Ene-Like Cycloisomerization Reaction of Nitrile Oxides with a Tethered Allyltrimethylsilyl Group Teruhiko Ishikawa Dr., Teruhiko Ishikawa Dr. Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorJin Urano, Jin Urano Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorShushiro Ikeda, Shushiro Ikeda Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorYasuhiro Kobayashi, Yasuhiro Kobayashi Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorSeiki Saito Prof., Seiki Saito Prof. [email protected] Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this author Teruhiko Ishikawa Dr., Teruhiko Ishikawa Dr. Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorJin Urano, Jin Urano Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorShushiro Ikeda, Shushiro Ikeda Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorYasuhiro Kobayashi, Yasuhiro Kobayashi Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this authorSeiki Saito Prof., Seiki Saito Prof. [email protected] Department of Bioscience and Biotechnology Faculty of Engineering, Okayama University Tsushima, Okayama, 700-8530, Japan, Fax: (+81) 86-251-8209Search for more papers by this author First published: 02 May 2002 https://doi.org/10.1002/1521-3773(20020503)41:9 3.0.CO;2-MCitations: 20 This work was supported by a Grant-in-Aid for Scientific research on Priority Areas (A) "Exploitation of Multi-Element Cyclic Molecules" from the Japanese Ministry of Education, Culture, Sports, Science, and Technology. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation 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 onFacebookTwitterLinkedInRedditWechat Graphical Abstract "I took the road less traveled by and that has made all the difference." Not only fans of the poet Robert Frost recognize the attraction of the less common reaction path. Rather than the expected [3+2] cycloaddition, a novel ene-like cycloisomerization occurs on deprotonation of allyltrimethylsilyl–oxime compounds when the β-sp2 carbon atom of the allyltrimethylsilyl moiety is tethered to the oxime unit (see scheme). The resulting nitrile oxide functional group serves as an enophile, and the final cyclized product still has two functional groups suitable for further manipulations. TMS=SiMe3. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z17943_s.pdf or from the author. 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. Volume41, Issue9May 3, 2002Pages 1586-1588 RelatedInformation