Asymmetrische nucleophile Glyoxylierung durch metallierte α‐Aminonitril‐Derivate in Michael‐Additionen an Nitroalkene
2007; Wiley; Volume: 119; Issue: 13 Linguagem: Alemão
10.1002/ange.200604802
ISSN1521-3757
AutoresDieter Enders, Maurice Hubert Bonten, Gerhard Raabe,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoAngewandte ChemieVolume 119, Issue 13 p. 2364-2367 Zuschrift Asymmetrische nucleophile Glyoxylierung durch metallierte α-Aminonitril-Derivate in Michael-Additionen an Nitroalkene† Dieter Enders Prof. Dr., Dieter Enders Prof. Dr. [email protected] Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Deutschland, Fax: (+49) 241-809-2127 http://www.oc.rwth-aachen.deSearch for more papers by this authorMaurice Hubert Bonten Dipl.-Chem., Maurice Hubert Bonten Dipl.-Chem. Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Deutschland, Fax: (+49) 241-809-2127 http://www.oc.rwth-aachen.deSearch for more papers by this authorGerhard Raabe Prof. Dr., Gerhard Raabe Prof. Dr. Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Deutschland, Fax: (+49) 241-809-2127 http://www.oc.rwth-aachen.deSearch for more papers by this author Dieter Enders Prof. Dr., Dieter Enders Prof. Dr. [email protected] Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Deutschland, Fax: (+49) 241-809-2127 http://www.oc.rwth-aachen.deSearch for more papers by this authorMaurice Hubert Bonten Dipl.-Chem., Maurice Hubert Bonten Dipl.-Chem. Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Deutschland, Fax: (+49) 241-809-2127 http://www.oc.rwth-aachen.deSearch for more papers by this authorGerhard Raabe Prof. Dr., Gerhard Raabe Prof. Dr. Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Deutschland, Fax: (+49) 241-809-2127 http://www.oc.rwth-aachen.deSearch for more papers by this author First published: 09 March 2007 https://doi.org/10.1002/ange.200604802Citations: 8 † Diese Arbeit wurde vom Fonds der Chemischen Industrie unterstützt. Wir danken der ehemaligen Firma Boehringer Mannheim GmbH, der BASF AG und der Bayer AG für Chemikalienspenden. Wir sind Dr. C. W. Lehmann, MPI Mülheim, dankbar für die Messung der Röntgendaten. 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 Effizient und selektiv: Eine asymmetrische nucleophile Glyoxylierung konnte erstmals durch metallierte Glyoxylat-Aminonitril-Derivate in Michael-Additionen an Nitroalkene erzielt werden. Nach Rücküberführung der Aminonitril- in die Ketofunktion unter Abspaltung des chiralen Auxiliars wurden die γ-Nitro-α-ketoester in guten Ausbeuten und mit exzellenten Enantiomerenüberschüssen erhalten (siehe Schema). Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2007/z604802_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. References 1Übersichtsartikel: Google Scholar 1aA. J. L. Cooper, J. Z. Ginos, A. Meister, Chem. Rev. 1983, 83, 321–358; 10.1021/cr00055a004 CASWeb of Science®Google Scholar 1bL. Kovacs, Recl. Trav. Chim. Pays-Bas 1993, 112, 471–496. 10.1002/recl.19931120902 CASWeb of Science®Google Scholar 2 2aT. D. Ocain, D. H. Rich, J. Med. Chem. 1992, 35, 451–456; 10.1021/jm00081a005 CASPubMedWeb of Science®Google Scholar 2bD. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, S. A. Smith, E. W. Petrillo, J. Med. Chem. 1993, 36, 2431–2447; 10.1021/jm00069a001 CASPubMedWeb of Science®Google Scholar 2cA. E. P. Adang, A. P. A. de Man, G. M. T. Vogel, P. D. J. Grootenhuis, M. J. Smit, C. A. M. Peters, A. Visser, J. B. M. Rewinkel, T. van Dinther, H. Lucas, J. Kelder, S. van Aelst, D. G. Meuleman, C. A. A. van Boeckel, J. Med. Chem. 2002, 45, 4419–4432. 10.1021/jm011110z CASPubMedWeb of Science®Google Scholar 3 3aW. Yuan, C.-H. Wong, J. Z. Haeggström, A. Wetterholm, B. Samuelsson, J. Am. Chem. Soc. 1992, 114, 6552–6553; 10.1021/ja00042a041 CASWeb of Science®Google Scholar 3bW. Yuan, B. Munoz, C.-H. Wong, J. Z. Haeggström, A. Wetterholm, B. Samuelsson, J. Med. Chem. 1993, 36, 211–220. 10.1021/jm00054a004 CASPubMedWeb of Science®Google Scholar 4Übersichtsartikel: M. J. Kiefel, M. von Itzstein, Chem. Rev. 2002, 102, 471–490. 10.1021/cr000414a CASPubMedWeb of Science®Google Scholar 5 5aD. M. Gordon, G. M. Whitesides, J. Org. Chem. 1993, 58, 7937–7938; 10.1021/jo00079a050 CASWeb of Science®Google Scholar 5bT.-H. Chan, M.-C. Lee, J. Org. Chem. 1995, 60, 4228–4232; 10.1021/jo00118a044 CASWeb of Science®Google Scholar 5cS. Jiang, A. D. Rycroft, G. Singh, X.-Z. Wang, Y.-L. Wu, Tetrahedron Lett. 1998, 39, 3809–3812. 10.1016/S0040-4039(98)00590-5 CASWeb of Science®Google Scholar 6 6aS. D. Burke, G. M. Sametz, Org. Lett. 1999, 1, 71–74; 10.1021/ol9905506 CASPubMedWeb of Science®Google Scholar 6bL.-S. Li, Y.-L. Wu, Y.-K. Wu, Org. Lett. 2000, 2, 891–894. 10.1021/ol0055418 CASPubMedWeb of Science®Google Scholar 7A. Kuboki, T. Tajimi, Y. Tokuda, D. Kato, T. Sugai, S. Ohira, Tetrahedron Lett. 2004, 45, 4545–4548. 10.1016/j.tetlet.2004.04.016 CASWeb of Science®Google Scholar 8Übersichtsartikel: Google Scholar 8aD. Seebach, Angew. Chem. 1969, 81, 690–700; 10.1002/ange.19690811707 Google ScholarAngew. Chem. Int. Ed. Engl. 1969, 8, 639–649. 10.1002/anie.196906391 CASWeb of Science®Google Scholar 9aT. Takahashi, T. Okano, T. Harada, K. Imamura, H. Yamada, Synlett 1994, 121–122; 10.1055/s-1994-22762 Web of Science®Google Scholar 9bH. Tsukamoto, T. Takahashi, Tetrahedron Lett. 1997, 38, 6415–6418. 10.1016/S0040-4039(97)01484-6 CASWeb of Science®Google Scholar 10M. Reiner, F. Stolz, R. R. Schmidt, Eur. J. Org. Chem. 2002, 57–60. 10.1002/1099-0690(20021)2002:1 3.0.CO;2-H CASWeb of Science®Google Scholar 11Einige Beispiele: Google Scholar 11aM. Amat, M. Pérez, N. Llor, J. Bosch, Org. Lett. 2002, 4, 2787–2790; 10.1021/ol0263245 CASPubMedWeb of Science®Google Scholar 11bM. Cushman, D. Yang, S. Gerhardt, R. Huber, M. Fischer, K. Kis, A. Bacher, J. Org. Chem. 2002, 67, 5807–5816; 10.1021/jo0201631 CASPubMedWeb of Science®Google Scholar 11cI. Coldham, K. M. Crapnell, J.-C. Fernàndez, J. D. Moseley, R. Rabot, J. Org. Chem. 2002, 67, 6181–6187. 10.1021/jo016376s CASPubMedWeb of Science®Google Scholar 12 12aD. Enders, H. Dyker, G. Raabe, Angew. Chem. 1992, 104, 649–651; 10.1002/ange.19921040535 CASGoogle ScholarAngew. Chem. Int. Ed. Engl. 1992, 31, 618–620; 10.1002/anie.199206181 Web of Science®Google Scholar 12bE. Tyrell, G. A. Skinner, J. Janes, G. Milsom, Synlett 2002, 1073–1076; 10.1055/s-2002-32574 Google Scholar 12cL. Abraham, M. Körner, P. Schwab, M. Hiersemann, Adv. Synth. Catal. 2004, 346, 1281–1294. 10.1002/adsc.200404051 CASWeb of Science®Google Scholar 13Struktur und Anwendungen metallierter chiraler Aminonitrile: Google Scholar 13aD. Enders, H. Lotter, Nouv. J. Chim. 1984, 8, 747–750; CASWeb of Science®Google Scholar 13bG. Raabe, E. Zobel, J. Fleischhauer, P. Gerdes, D. Mannes, E. Müller, D. Enders, Z. Naturforsch. A 1991, 46, 275–288; 10.1515/zna-1991-0311 CASWeb of Science®Google Scholar 13cD. Enders, J. Kirchhoff, P. Gerdes, D. Mannes, G. Raabe, J. Runsink, G. Boche, M. Marsch, H. Ahlbrecht, H. Sommer, Eur. J. Org. Chem. 1998, 63–72; 10.1002/(SICI)1099-0690(199801)1998:1 3.0.CO;2-H CASWeb of Science®Google Scholar 13dD. Enders, J. P. Shilvock, G. Raabe, J. Chem. Soc. Perkin 1 1999, 1617–1620; 10.1039/a903536b CASWeb of Science®Google Scholar 13eÜbersichtsartikel: D. Enders, J. P. Shilvock, Chem. Soc. Rev. 2000, 29, 359–373. 10.1039/a908290e CASWeb of Science®Google Scholar 14Übersichtsartikel: Google Scholar 14aD. Seebach, Angew. Chem. 1979, 91, 259–285; 10.1002/ange.19790910404 CASGoogle ScholarAngew. Chem. Int. Ed. Engl. 1979, 18, 239–264; 10.1002/anie.197902393 Web of Science®Google Scholar 14bD. J. Ager in Umpoled Synthons (Hrsg.: ), Wiley, New York, 1987, S. 19–72. Google Scholar 15 15aD. Enders, D. Mannes, G. Raabe, Synlett 1992, 837–839; 10.1055/s-1992-21511 CASWeb of Science®Google Scholar 15bD. Enders, J. Kirchhoff, D. Mannes, G. Raabe, Synthesis 1995, 659–666; 10.1055/s-1995-3968 CASWeb of Science®Google Scholar 15cD. Enders, J. Kirchhoff, V. Lausberg, Liebigs Ann. 1996, 1361–1366; CASWeb of Science®Google Scholar 15dD. Enders, V. Lausberg, G. D. Signore, O. M. Berner, Synthesis 2002, 515–522; 10.1055/s-2002-20967 CASWeb of Science®Google Scholar 15eD. E. Enders, G. D. Signore, O. M. Berner, Chirality 2003, 15, 510–513; 10.1002/chir.10242 CASPubMedWeb of Science®Google Scholar 15fD. Enders, M. Milovanovic, E. Voloshina, G. Raabe, J. Fleischhauer, Eur. J. Org. Chem. 2005, 1984–1990; 10.1002/ejoc.200400885 CASWeb of Science®Google Scholar 15gD. Enders, M. Milovanovic, Z. Naturforsch. B 2007, 62b, 117–120. Google Scholar 16 16aD. Enders, P. Gerdes, H. Kipphardt, Angew. Chem. 1990, 102, 226–228; 10.1002/ange.19901020228 CASGoogle ScholarAngew. Chem. Int. Ed. Engl. 1990, 29, 179–181. 10.1002/anie.199001791 Web of Science®Google Scholar 17Ein Kurzaufsatz über Eigenschaften und Anwendungen von Glyoxylaten in der Chemie: W. J. N. Meester, J. H. van Maarseveen, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2003, 2519–2529. 10.1002/ejoc.200200714 CASWeb of Science®Google Scholar 18H. Kipphardt, Dissertation, RWTH Aachen, 1986. Google Scholar 19J. P. Albarella, J. Org. Chem. 1977, 42, 2009–2010. 10.1021/jo00431a040 CASWeb of Science®Google Scholar 20Übersichtsartikel: O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877–1894. 10.1002/1099-0690(200206)2002:12 3.0.CO;2-U CASWeb of Science®Google Scholar 21 21aD. Seebach, E. W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1–18; CASWeb of Science®Google Scholar 21bG. Calderari, D. Seebach, Helv. Chim. Acta 1995, 78, 1592–1604. Google Scholar 22 22aD. Förster, unveröffentlichte Ergebnisse; Google Scholar 22bD. Enders, D. Förster, G. Raabe, J. W. Bats, Manuskript in Vorbereitung. Google Scholar 23CCDC 290371 enthält die ausführlichen kristallographischen Daten zu dieser Veröffentlichung. Die Daten sind kostenlos beim Cambridge Crystallographic Data Centre über www.ccdc.cam.ac.uk/data_request/cif erhältlich. Google Scholar Citing Literature Volume119, Issue13March 19, 2007Pages 2364-2367 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
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