Enantioselective Synthesis of Trifluoromethyl‐Substituted 2‐Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction
2010; Wiley; Volume: 122; Issue: 33 Linguagem: Inglês
10.1002/ange.201002065
ISSN1521-3757
AutoresKazutaka Matoba, Hiroyuki Kawai, Tatsuya Furukawa, Akihiro Kusuda, Etsuko Tokunaga, Shuichi Nakamura, Motoo Shiro, Norio Shibata,
Tópico(s)Synthesis and Reactions of Organic Compounds
ResumoAngewandte ChemieVolume 122, Issue 33 p. 5898-5902 Zuschrift Enantioselective Synthesis of Trifluoromethyl-Substituted 2-Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction† Kazutaka Matoba, Kazutaka Matoba Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorHiroyuki Kawai, Hiroyuki Kawai Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorTatsuya Furukawa, Tatsuya Furukawa Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorAkihiro Kusuda, Akihiro Kusuda Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorEtsuko Tokunaga, Etsuko Tokunaga Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorShuichi Nakamura Dr., Shuichi Nakamura Dr. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorMotoo Shiro Dr., Motoo Shiro Dr. Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima Tokyo 196-8666 (Japan)Search for more papers by this authorNorio Shibata Prof., Norio Shibata Prof. [email protected] Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this author Kazutaka Matoba, Kazutaka Matoba Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorHiroyuki Kawai, Hiroyuki Kawai Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorTatsuya Furukawa, Tatsuya Furukawa Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorAkihiro Kusuda, Akihiro Kusuda Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorEtsuko Tokunaga, Etsuko Tokunaga Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorShuichi Nakamura Dr., Shuichi Nakamura Dr. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this authorMotoo Shiro Dr., Motoo Shiro Dr. Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima Tokyo 196-8666 (Japan)Search for more papers by this authorNorio Shibata Prof., Norio Shibata Prof. [email protected] Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442Search for more papers by this author First published: 28 July 2010 https://doi.org/10.1002/ange.201002065Citations: 41 † Support was provided by KAKENHI (21390030, 22106515). The corresponding author thanks the JSPS for financial support of this work in part through a Joint Research Project between Japan and France. 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 Eine Sequenz von Addition, Cyclisierung und Dehydrierung liefert die biologisch wichtigen chiralen 3,5-Diaryl-5-(trifluormethyl)-2-isoxazoline 1 in hervorragenden Ausbeuten und hohen Enantioselektivitäten. Der gezielte Zugang zum S- oder R-Enantiomer der Produkte wurde durch die Wahl eines geeigneten Phasentransferkatalysators (2) eröffnet. 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_201002065_sm_miscellaneous_information.pdf14.3 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 1 1aV. A. Petrov, Fluorinated Heterocyclic Compounds: Synthesis Chemistry, and Applications, Wiley, Hoboken, NJ, 2009; 10.1002/9780470528952 Google Scholar 1bP. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004; 10.1002/352760393X Google Scholar 1cI. 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These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif). Google Scholar Citing Literature Volume122, Issue33August 2, 2010Pages 5898-5902 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
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