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The Synthesis of Highly Substituted Cyclooctatetraene Scaffolds by Metal‐Catalyzed [2+2+2+2] Cycloadditions: Studies on Regioselectivity, Dynamic Properties, and Metal Chelation

2009; Wiley; Volume: 121; Issue: 41 Linguagem: Inglês

10.1002/ange.200903859

1521-3757

Paul A. Wender, Justin P. Christy, Adam B. Lesser, Marc Timo Gieseler,

Catalytic Alkyne Reactions

Angewandte ChemieVolume 121, Issue 41 p. 7823-7826 Zuschrift The Synthesis of Highly Substituted Cyclooctatetraene Scaffolds by Metal-Catalyzed [2+2+2+2] Cycloadditions: Studies on Regioselectivity, Dynamic Properties, and Metal Chelation† Paul A. Wender Prof., Paul A. Wender Prof. [email protected] Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this authorJustin P. Christy, Justin P. Christy Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this authorAdam B. Lesser, Adam B. Lesser Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this authorMarc T. Gieseler, Marc T. Gieseler Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this author Paul A. Wender Prof., Paul A. Wender Prof. [email protected] Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this authorJustin P. Christy, Justin P. Christy Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this authorAdam B. Lesser, Adam B. Lesser Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this authorMarc T. Gieseler, Marc T. Gieseler Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650-725-0259 http://www.stanford.edu/group/pawender/Search for more papers by this author First published: 23 September 2009 https://doi.org/10.1002/ange.200903859Citations: 21 † This research was supported by a grant (CHE-0450638) from the National Science Foundation. J.P.C and A.B.L. thank Amgen for financial support. M.T.G thanks the Deutscher Akademischer Austauschdienst for financial support. We thank Allen Oliver at the University of California, Santa Cruz and Prateek Verma at Stanford University for X-ray crystal structures. We also thank Kristen Brownell for assisting in substrate preparation. 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 Ni0-katalysierte [2+2+2+2]-Cycloaddition von 1,6-Diinen liefert hoch funktionalisierte sechs- und achtfach substituierte Cyclooctatetraene (COTs) (siehe Bild), darunter das erste Beispiel für das Produkt einer vollständig intramolekularen [2+2+2+2]-Cycloaddition. Die Regioselektivität dieses Prozesses wird untersucht, und die erste Verwendung eines COT-Liganden wird am Beispiel eines Bisoxazolin-COT-Komplexes von ZnII aufgezeigt (rechts). 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. 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