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Donor–Acceptor Cyclopropanes as Three‐Carbon Components in a [4+3] Cycloaddition Reaction with 1,3‐Diphenylisobenzofuran

2008; Wiley; Volume: 47; Issue: 6 Linguagem: Inglês

10.1002/anie.200704438

ISSN

1521-3773

Autores

Оlga А. Ivanova, Екатерина М. Будынина, Yuri K. Grishin, Igor V. Trushkov, Pavel V. Verteletskii,

Tópico(s)

Synthetic Organic Chemistry Methods

Resumo

Angewandte Chemie International EditionVolume 47, Issue 6 p. 1107-1110 Communication Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran Olga A. Ivanova Dr., Olga A. Ivanova Dr. [email protected] Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorEkaterina M. Budynina Dr., Ekaterina M. Budynina Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorYuri K. Grishin Dr., Yuri K. Grishin Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorIgor V. Trushkov Dr., Igor V. Trushkov Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorPavel V. Verteletskii Dr., Pavel V. Verteletskii Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this author Olga A. Ivanova Dr., Olga A. Ivanova Dr. [email protected] Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorEkaterina M. Budynina Dr., Ekaterina M. Budynina Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorYuri K. Grishin Dr., Yuri K. Grishin Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorIgor V. Trushkov Dr., Igor V. Trushkov Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this authorPavel V. Verteletskii Dr., Pavel V. Verteletskii Dr. Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1–3, Moscow 119992, Russia, Fax: (+7) 495-939-3969Search for more papers by this author First published: 21 January 2008 https://doi.org/10.1002/anie.200704438Citations: 148Read 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 Graphical Abstract Dienophiles with a difference: 2-Aryl 1,1-bis(alkoxycarbonyl) cyclopropanes undergo the title reaction under the catalysis of ytterbium triflate (Yb(OTf)3) in excellent yield (see scheme). Under mild reaction conditions, the major product is the less stable exo isomer. At higher temperatures, the endo isomer is obtained exclusively, as the exo cycloadduct decomposes through cycloreversion. References 1 1a The Chemistry of the Cyclopropyl Group, Vol. 1 (Ed.: ), Wiley, New York, 1987; 1b The Chemistry of the Cyclopropyl Group, Vol. 2 (Ed.: ), Wiley, New York, 1995. 2A. de Meijere, Angew. Chem. 1979, 91, 867– 884; Angew. Chem. Int. Ed. Engl. 1979, 18, 809– 826. 3For reviews on the reactivity of electrophilic cyclopropanes, see: 3aS. Danishefsky, Acc. Chem. Res. 1979, 12, 66– 72; 3bR. Verhe, N. de Kimpe in The Chemistry of the Cyclopropyl Group, Vol. 1 (Ed.: ), Wiley, Chichester, 1987, pp. 445– 564; 3c"Carbocyclic Three- and Four-Membered Ring Compounds": S. Angerer in Houben-Weyl, Methods of Organic Chemistry, Vol. E17c (Ed.: ), Thieme, Stuttgart, 1997, pp. 2041– 2120. 4T. Tsuji, S. Nishida, Acc. Chem. 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Ed. 2003, 42, 3023– 3026; 13bM. D. Ganton, M. A. Kerr, J. Org. Chem. 2004, 69, 8554– 8557; 13cI. S. Young, M. A. Kerr, Org. Lett. 2004, 6, 139– 141; 13dI. S. Young, J. L. Williams, M. A. Kerr, Org. Lett. 2005, 7, 953– 955; 13eF. Cardona, A. Goti, Angew. Chem. 2005, 117, 8042– 8045; Angew. Chem. Int. Ed. 2005, 44, 7832– 7835; 13fM. P. Sibi, Z. Ma, C. P. Jasperse, J. Am. Chem. Soc. 2005, 127, 5764– 5765; 13gY.-B. Kang, X.-L. Sun, Y. Tang, Angew. Chem. 2007, 119, 3992– 3995; Angew. Chem. Int. Ed. 2007, 46, 3918– 3921. 14C. A. Carson, M. A. Kerr, J. Org. Chem. 2005, 70, 8242– 8244. 15V. S. Korotkov, O. V. Larionov, A. de Meijere, Synthesis 2006, 3542– 3546. 16For details, see the Supporting Information. 17CCDC 654178 (3 b) and 654179 (4 b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z704438_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. Volume47, Issue6January 25, 2008Pages 1107-1110 ReferencesRelatedInformation

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