Divergent Mechanisms for the Skeletal Rearrangement and [2+2] Cycloaddition of Enynes Catalyzed by Gold
Unterstützung für die direkte Route: DFT‐Rechnungen und kinetische Studien deuten an, dass Cyclobutene nicht notwendigerweise als Intermediate der Gerüstumlagerungen von Eninen auftreten. Die Cyclobutene können aus den entsprechenden syn‐Cyclopropylgold(I)‐Carbenen entstehen (siehe Schema)....
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| Published in | Angewandte Chemie Vol. 117; no. 38; pp. 6302 - 6304 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
26.09.2005
WILEY‐VCH Verlag |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0044-8249 1521-3757 |
| DOI | 10.1002/ange.200501937 |
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| Abstract | Unterstützung für die direkte Route: DFT‐Rechnungen und kinetische Studien deuten an, dass Cyclobutene nicht notwendigerweise als Intermediate der Gerüstumlagerungen von Eninen auftreten. Die Cyclobutene können aus den entsprechenden syn‐Cyclopropylgold(I)‐Carbenen entstehen (siehe Schema). |
|---|---|
| AbstractList | Unterstützung für die direkte Route: DFT‐Rechnungen und kinetische Studien deuten an, dass Cyclobutene nicht notwendigerweise als Intermediate der Gerüstumlagerungen von Eninen auftreten. Die Cyclobutene können aus den entsprechenden syn‐Cyclopropylgold(I)‐Carbenen entstehen (siehe Schema). |
| Author | Muñoz, M. Paz Nevado, Cristina Cárdenas, Diego J. Nieto-Oberhuber, Cristina López, Salomé Buñuel, Elena Echavarren, Antonio M. |
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| Notes | ArticleID:ANGE200501937 istex:867C319FA4A3562C9F7456D36EF689E1699A4CF1 ark:/67375/WNG-54RJCCLX-1 This work was supported by the MEC (project CTQ2004-02869, predoctoral fellowships to C.N.-O. and M.P.M., and a Torres Quevedo contract to S.L.), the CAM (predoctoral fellowship to C.N.), and the ICIQ Foundation. We also thank the Centro de Computación Científica (UAM), and Johnson Matthey PLC. This work was supported by the MEC (project CTQ2004‐02869, predoctoral fellowships to C.N.‐O. and M.P.M., and a Torres Quevedo contract to S.L.), the CAM (predoctoral fellowship to C.N.), and the ICIQ Foundation. We also thank the Centro de Computación Científica (UAM), and Johnson Matthey PLC. |
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| References_xml | – reference: C. H. Oh, S. Y. Bang, C. Y. Rhim, Bull. Korean Chem. Soc. 2003, 24, 887-888. – reference: B. M. Trost, M. Yanai, K. Hoogsteed, J. Am. Chem. Soc. 1993, 115, 5294-5295; – reference: G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215-236; – reference: G. Oba, G. Moreira, G. Manuel, M. Koenig, J. Organomet. Chem. 2002, 643-644, 324-330. – reference: S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382; – reference: M. P. Muñoz, J. Adrio, J. C. Carretero, A. M. Echavarren, Organometallics 2005, 24, 1293-1300. – reference: N. Chatani, H. Inoue, T. Morimoto, T. Muto, S. Murai, J. Org. Chem. 2001, 66, 4433-4436; – reference: The thermal ring-opening of a cyclobutene formed in a reaction of an enyne catalyzed by PtBr2 has been shown to take place at 120 °C in acetonitrile: G. B. Bajracharya, I. Nakamura, Y. Yamamoto, J. Org. Chem. 2005, 70, 892-897. – reference: D. J. Tantillo, R. Hoffmann, J. Am. Chem. Soc. 2001, 123, 9855-9859. – reference: A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863-11869; – reference: M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858-10859. – reference: V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655; – reference: B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1988, 110, 1636-1638; – reference: M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; – reference: C. Nieto-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179. – reference: P. N. Dickson, A. Wehrli, G. Geier, Inorg. Chem. 1988, 27, 2921-2925. – reference: C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460; – reference: L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 11806-11807; – reference: P. S. Lee, S. Sakai, P. Hörstermann, W. R. Roth, E. A. Kallel, K. N. Houk, J. Am. Chem. 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| SubjectTerms | Alkine Cyclisierungen Dichtefunktionalrechnungen Gold Umlagerungen |
| Title | Divergent Mechanisms for the Skeletal Rearrangement and [2+2] Cycloaddition of Enynes Catalyzed by Gold |
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