Ring Expansion and Rearrangements of Rhodium(II) Azavinyl Carbenes
2012; Wiley; Volume: 124; Issue: 52 Linguagem: Inglês
10.1002/ange.201207820
ISSN1521-3757
AutoresNicklas Selander, Brady T. Worrell, Valery V. Fokin,
Tópico(s)Synthesis and Catalytic Reactions
ResumoAngewandte ChemieVolume 124, Issue 52 p. 13231-13234 Zuschrift Ring Expansion and Rearrangements of Rhodium(II) Azavinyl Carbenes† Dr. Nicklas Selander, Dr. Nicklas Selander Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinSearch for more papers by this authorBrady T. Worrell, Brady T. Worrell Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinSearch for more papers by this authorDr. Valery V. Fokin, Corresponding Author Dr. Valery V. Fokin [email protected] Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinSearch for more papers by this author Dr. Nicklas Selander, Dr. Nicklas Selander Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinSearch for more papers by this authorBrady T. Worrell, Brady T. Worrell Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinSearch for more papers by this authorDr. Valery V. Fokin, Corresponding Author Dr. Valery V. Fokin [email protected] Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/fokinSearch for more papers by this author First published: 19 November 2012 https://doi.org/10.1002/ange.201207820Citations: 48 † This work was supported by the National Science Foundation (CHE-0848982) and the National Institute of General Medical Science, National Institutes of Health (GM-087620). N.S. also acknowledges a postdoctoral fellowship from the Swedish Research Council (VR). Dr. Jessica Raushel’s contribution to the initial ring-expansion studies is gratefully acknowledged. 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 Wenn der Ring zu klein wird: Eine regioselektive und konvergente Methode für Ringerweiterung und Umlagerung von 1-Sulfonyl-1,2,3-triazolen unter Rhodium(II)-Katalyse und N2-Abspaltung zu substituierten Enaminonen und Olefinen wurde entwickelt (siehe Schema). Die Enaminon-Produkte können anschließend in verschiedene Heterocyclen und Ketonderivate umgewandelt werden, aus denen das Sulfonyltriazol spurlos verschwindet. 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_201207820_sm_miscellaneous_information.pdf7.5 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 1Rhodium(II)-catalyzed ring expansions: Google Scholar 1aA. Padwa, Y. S. Kulkarni, Z. Zhang, J. Org. Chem. 1990, 55, 4144; 10.1021/jo00300a035 CASWeb of Science®Google Scholar 1bR. Pellicciari, B. Natalini, B. M. Sadeghpour, M. Marinozzi, J. P. Snyder, B. L. Williamson, J. T. Kuethe, A. Padwa, J. Am. Chem. Soc. 1996, 118, 1; 10.1021/ja950971s CASWeb of Science®Google Scholar 1cD. Damour, A. Renaudon, S. 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