Highly Enantioselective Catalytic [6+3] Cycloadditions of Azomethine Ylides†
Correction(s) for this article
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Berichtigung: Highly Enantioselective Catalytic [6+3] Cycloadditions of Azomethine Ylides
- Volume 125Issue 29Angewandte Chemie
- pages: 7484-7484
- First Published online: July 11, 2013
Marco Potowski
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät Chemie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorJonathan O. Bauer
Technische Universität Dortmund, Fakultät Chemie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorProf. Dr. Carsten Strohmann
Technische Universität Dortmund, Fakultät Chemie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorCorresponding Author
Dr. Andrey P. Antonchick
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)Search for more papers by this authorCorresponding Author
Prof. Dr. Herbert Waldmann
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät Chemie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)Search for more papers by this authorMarco Potowski
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät Chemie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorJonathan O. Bauer
Technische Universität Dortmund, Fakultät Chemie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorProf. Dr. Carsten Strohmann
Technische Universität Dortmund, Fakultät Chemie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorCorresponding Author
Dr. Andrey P. Antonchick
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)Search for more papers by this authorCorresponding Author
Prof. Dr. Herbert Waldmann
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät Chemie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)Search for more papers by this authorM.P. and J.O.B. thank the Fonds der Chemischen Industrie for a fellowship.
Graphical Abstract
Unter Kontrolle: Hoch funktionalisierte chirale anellierte Piperidinderivate mit acht Stereozentren bilden sich effizient über eine hoch enantioselektive [6+3]/[4+2]-Eintopfsequenz. Teil dieser Sequenz ist die erste enantioselektive [6+3]-Cycloaddition von Azomethin-Yliden mit Fulvenen.
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References
- 1
- 1aK. Kumar, H. Waldmann, Angew. Chem. 2009, 121, 3272–3290; Angew. Chem. Int. Ed. 2009, 48, 3224–3242;
- 1bM. Kaiser, S. Wetzel, K. Kumar, H. Waldmann, Cell. Mol. Life Sci. 2008, 65, 1186–1201;
- 1cR. S. Bon, H. Waldmann, Acc. Chem. Res. 2010, 43, 1103–1114;
- 1dS. Wetzel, R. S. Bon, K. Kumar, H. Waldmann, Angew. Chem. 2011, 123, 10990–11018;
10.1002/ange.201007004 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 10800–10826.
- 2For reviews, see
- 2aH. Pellissier, Tetrahedron 2012, 68, 2197–2232;
- 2bA. Sakakura, K. Ishihara, Chem. Soc. Rev. 2011, 40, 163–172;
- 2cH. Pellissier, Adv. Synth. Catal. 2011, 353, 189–218;
- 2dA. Moyano, R. Rios, Chem. Rev. 2011, 111, 4703–4832;
- 2eG. Domínguez, J. Pérez-Castells, Chem. Soc. Rev. 2011, 40, 3430–3444;
- 2fH. Pellissier, Tetrahedron 2010, 66, 1509–1555;
- 2gB. Alcaide, P. Almendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783–816;
- 2hS. Perreault, T. Rovis, Chem. Soc. Rev. 2009, 38, 3149–3159;
- 2iH. Pellissier, Tetrahedron 2009, 65, 2839–2877;
- 2jP. Wessig, G. Muller, Chem. Rev. 2008, 108, 2051–2063;
- 2kS. Reymond, J. Cossy, Chem. Rev. 2008, 108, 5359–5406;
- 2lT. Shibata, Adv. Synth. Catal. 2006, 348, 2328–2336;
- 2mM. Harmata, Adv. Synth. Catal. 2006, 348, 2297–2306;
- 2nR. P. Hsung, A. V. Kurdyumov, N. Sydorenko, Eur. J. Org. Chem. 2004, 23–44;
- 2oE. J. Corey, Angew. Chem. 2002, 114, 1724–1741;
10.1002/1521-3757(20020517)114:10<1724::AID-ANGE1724>3.0.CO;2-Q Google ScholarAngew. Chem. Int. Ed. 2002, 41, 1650–1667.10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO;2-B CAS PubMed Web of Science® Google Scholar
- 3For reviews, see
- 3aJ. Adrio, J. C. Carretero, Chem. Commun. 2011, 47, 6784–6794;
- 3bC. Nájera, J. M. Sansano, M. Yus, J. Braz. Chem. Soc. 2010, 21, 377–412;
- 3cL. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887–2902;
- 3dH. Pellissier, Tetrahedron 2007, 63, 3235–3285;
- 3eV. Nair, T. D. Suja, Tetrahedron 2007, 63, 12247–12275;
- 3fG. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484–4517;
- 3gC. Nájera, J. M. Sansano, Angew. Chem. 2005, 117, 6428–6432;
10.1002/ange.200501074 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 6272–6276;
- 3hI. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765–2809.
- 4For selected recent examples on [3+2] cycloadditions of azomethine ylides, see:
- 4aE. Conde, D. Bello, A. de Cózar, M. Sánchez, M. A. Vázquez, F. P. Cossío, Chem. Sci. 2012, 3, 1486–1491;
- 4bM. González-Esguevillas, J. Adrio, J. C. Carretero, Chem. Commun. 2012, 48, 2149–2151;
- 4cT.-L. Liu, Z.-L. He, Q.-H. Li, H.-Y. Tao, C.-J. Wang, Adv. Synth. Catal. 2011, 353, 1713–1719;
- 4dY. Yamashita, T. Imaizumi, S. Kobayashi, Angew. Chem. 2011, 123, 4995–4998; Angew. Chem. Int. Ed. 2011, 50, 4893–4896;
- 4eQ.-H. Li, M.-C. Tong, J. Li, H.-Y. Tao, C.-J. Wang, Chem. Commun. 2011, 47, 11110–11112;
- 4fT.-L. Liu, Z.-L. He, C.-J. Wang, Chem. Commun. 2011, 47, 9600–9602;
- 4gH.-L. Teng, H. Huang, H.-Y. Tao, C.-J. Wang, Chem. Commun. 2011, 47, 5494–5496;
- 4hT.-L. Liu, Z.-L. He, H.-Y. Tao, Y.-P. Cai, C.-J. Wang, Chem. Commun. 2011, 47, 2616–2618;
- 4iT. Arai, N. Yokoyama, A. Mishiro, H. Sato, Angew. Chem. 2010, 122, 8067–8070;
10.1002/ange.201004098 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 7895–7898;
- 4jZ.-Y. Xue, T.-L. Liu, Z. Lu, H. Huang, H.-Y. Tao, C.-J. Wang, Chem. Commun. 2010, 46, 1727–1729;
- 4kT. Arai, A. Mishiro, N. Yokoyama, K. Suzuki, H. Sato, J. Am. Chem. Soc. 2010, 132, 5338–5339;
- 4lI. Oura, K. Shimizu, K. Ogata, S.-i. Fukuzawa, Org. Lett. 2010, 12, 1752–1755;
- 4mC. Zhang, S.-B. Yu, X.-P. Hu, D.-Y. Wang, Z. Zheng, Org. Lett. 2010, 12, 5542–5545.
- 5For examples from our group, see
- 5aM. Potowski, M. Schurmann, H. Preut, A. P. Antonchick, H. Waldmann, Nat. Chem. Biol. 2012, 8, 428–430;
- 5bA. P. Antonchick, H. Schuster, H. Bruss, M. Schurmann, H. Preut, D. Rauh, H. Waldmann, Tetrahedron 2011, 67, 10195–10202;
- 5cA. P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schurmann, H. Preut, S. Ziegler, D. Rauh, H. Waldmann, Nat. Chem. 2010, 2, 735–740;
- 5dH. Waldmann, E. Blaser, M. Jansen, H. P. Letschert, Chem. Eur. J. 1995, 1, 150–154;
- 5eH. Waldmann, E. Blaser, M. Jansen, H. P. Letschert, Angew. Chem. 1994, 106, 717–719; Angew. Chem. Int. Ed. Engl. 1994, 33, 683–685.
- 6
- 6aY. Hayashi, H. Gotoh, M. Honma, K. Sankar, I. Kumar, H. Ishikawa, K. Konno, H. Yui, S. Tsuzuki, T. Uchimaru, J. Am. Chem. Soc. 2011, 133, 20175–20185;
- 6bB. M. Trost, P. J. McDougall, O. Hartmann, P. T. Wathen, J. Am. Chem. Soc. 2008, 130, 14960–14961;
- 6cR. Shintani, M. Murakami, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 12356–12357;
- 6dR. P. Reddy, H. M. L. Davies, J. Am. Chem. Soc. 2007, 129, 10312–10313;
- 6eM. Harmata, S. K. Ghosh, X. C. Hong, S. Wacharasindhu, P. Kirchhoefer, J. Am. Chem. Soc. 2003, 125, 2058–2059; for review, see
- 6fP. A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791–2805;
- 6gZ. X. Yu, Y. Wang, Y. Y. Wang, Chem. Asian J. 2010, 5, 1072–1088.
- 7B. C. Hong, A. K. Gupta, M. F. Wu, J. H. Liao, G. H. Lee, Org. Lett. 2003, 5, 1689–1692.
- 8Functionalized piperidines are important building blocks in organic synthesis and the development of novel methods for their synthesis is in high demand:
- 8aM. S. M. Pearson, M. Mathe-Allainmat, V. Fargeas, J. Lebreton, Eur. J. Org. Chem. 2005, 2159–2191;
- 8bM. G. P. Buffat, Tetrahedron 2004, 60, 1701–1729;
- 8cP. M. Weintraub, J. S. Sabol, J. A. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953–2989;
- 8dF. X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693–3712;
- 8eD. O’Hagan, Nat. Prod. Rep. 2000, 17, 435–446;
- 8fS. Laschat, T. Dickner, Synthesis 2000, 1781–1813.
- 9
- 9aJ. Priego, O. G. Mancheno, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, Chem. Commun. 2002, 2512–2513;
- 9bO. G. Mancheño, R. Gómez Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2004, 126, 456–457;
- 9cS. Cabrera, R. G. Arrayas, J. C. Carretero, Angew. Chem. 2004, 116, 4034–4037;
10.1002/ange.200460087 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 3944–3947;
- 9dS. Cabrera, R. G. Arrayas, J. C. Carretero, J. Am. Chem. Soc. 2005, 127, 16394–16395;
- 9eS. Cabrera, R. G. Arrayas, B. Martin-Matute, F. P. Cossio, J. C. Carretero, Tetrahedron 2007, 63, 6587–6602; and references [5a] and [5b].
- 10The products of the [6+3] cycloadditions are unstable during storage at low temperature owing to isomerization and dimerization. The products of the subsequent cycloaddition are considerably more stable.
- 11CCDC 885432 (6 aa) contains 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
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