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Are β‐Acylaminoacrylates Hydrogenated in the Same Way as α‐Acylaminoacrylates?

2004; Wiley; Volume: 44; Issue: 8 Linguagem: Inglês

10.1002/anie.200461716

ISSN

1521-3773

Autores

Hans‐Joachim Drexler, Wolfgang Baumann, Thomas Schmidt, Songlin Zhang, Ailing Sun, Anke Spannenberg, Christine Fischer, Helmut Buschmann, Detlef Heller,

Tópico(s)

Asymmetric Hydrogenation and Catalysis

Resumo

Angewandte Chemie International EditionVolume 44, Issue 8 p. 1184-1188 Communication Are β-Acylaminoacrylates Hydrogenated in the Same Way as α-Acylaminoacrylates?† Hans-Joachim Drexler Dr., Hans-Joachim Drexler Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorWolfgang Baumann Dr., Wolfgang Baumann Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorThomas Schmidt Dipl.-Chem., Thomas Schmidt Dipl.-Chem. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorSonglin Zhang Dr., Songlin Zhang Dr. College of Chemistry and Environmental Science, Henan Normal University Xinxiang, 453007 Henan, ChinaSearch for more papers by this authorAiling Sun Dr., Ailing Sun Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorAnke Spannenberg Dr., Anke Spannenberg Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorChristine Fischer Dr., Christine Fischer Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorHelmut Buschmann Dr., Helmut Buschmann Dr. ESTEVE, Av. Mare de Deu de Montserrat 221, 08041 Barcelona, SpainSearch for more papers by this authorDetlef Heller Priv.-Doz. Dr., Detlef Heller Priv.-Doz. Dr. [email protected] Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this author Hans-Joachim Drexler Dr., Hans-Joachim Drexler Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorWolfgang Baumann Dr., Wolfgang Baumann Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorThomas Schmidt Dipl.-Chem., Thomas Schmidt Dipl.-Chem. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorSonglin Zhang Dr., Songlin Zhang Dr. College of Chemistry and Environmental Science, Henan Normal University Xinxiang, 453007 Henan, ChinaSearch for more papers by this authorAiling Sun Dr., Ailing Sun Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorAnke Spannenberg Dr., Anke Spannenberg Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorChristine Fischer Dr., Christine Fischer Dr. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this authorHelmut Buschmann Dr., Helmut Buschmann Dr. ESTEVE, Av. Mare de Deu de Montserrat 221, 08041 Barcelona, SpainSearch for more papers by this authorDetlef Heller Priv.-Doz. Dr., Detlef Heller Priv.-Doz. Dr. [email protected] Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. Buchbinderstrasse 5/6, 18055 Rostock, Germany, Fax: (+49) 381-466-9383Search for more papers by this author First published: 04 February 2005 https://doi.org/10.1002/anie.200461716Citations: 45 † We thank the Deutsche Forschungsgemeinschaft for their generous support as well as Prof. C. R. Landis for stimulating discussions. We especially thank C. Pribbenow for skilled technical assistance. Read 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Five catalyst–substrate complexes of the type [Rh(chiral ligand)(β-dehydroamino acid derivative)]BF4 were characterized for the first time by X-ray analysis (see example). Low-temperature NMR spectroscopy proved that three of these complexes are “major” substrate complexes, which lead to the main product in asymmetric hydrogenation, contrary to the known classical examples with analogous α-dehydroamino acid derivatives. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z461716_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 1 1aJ.-A. Ma, Angew. Chem. 2003, 115, 4426–4435; 10.1002/ange.200301600 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 4290–4299; 10.1002/anie.200301600 CASPubMedWeb of Science®Google Scholar 1bN. Sewald, Angew. Chem. 2003, 115, 5972–5973; 10.1002/ange.200301692 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 5794–5795. 10.1002/anie.200301692 CASPubMedWeb of Science®Google Scholar 2Review: H.-J. Drexler, J. You, S. Zhang, C. Fischer, W. Baumann, A. Spannenberg, D. Heller, Org. Process Res. Dev. 2003, 7, 355–361. 10.1021/op034011z CASWeb of Science®Google Scholar 3 3aW. Tang, W. Wang, Y. Chi, X. Zhang, Angew. Chem. 2003, 115, 3633–3635; 10.1002/ange.200351465 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 3509–3511; 10.1002/anie.200351465 CASPubMedWeb of Science®Google Scholar 3bJ. You, H.-J. Drexler, S. Zhang, C. Fischer, D. Heller, Angew. Chem. 2003, 115, 942–945; 10.1002/ange.200390211 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 913–916; 10.1002/anie.200390242 PubMedWeb of Science®Google Scholar 3cD. Pena, A. J. Minnaard, J. G. deVries, B. L. Feringa, J. Am. Chem. Soc. 2002, 124, 14 552–14 553; 10.1021/ja028235t CASWeb of Science®Google Scholar 3dY.-G. Zhou, W. Tang, W.-B. Wang, W. Li, X. Zhang, J. Am. Chem. Soc. 2002, 124, 4952–4953. 10.1021/ja020121u CASPubMedWeb of Science®Google Scholar 4 4aA. S. C. Chan, J. J. Pluth, J. Halpern, J. Am. Chem. Soc. 1980, 102, 5952–5954; 10.1021/ja00538a064 CASWeb of Science®Google Scholar 4bJ. M. Brown, P. A. Chaloner, J. Chem. Soc. Chem. Commun. 1980, 344–346; 10.1039/c39800000344 CASWeb of Science®Google Scholar 4cJ. Halpern in Asymmetric Synthesis, Vol. 5 (Ed.: ), Academic Press, Orlando, 1985, pp. 41–69; 10.1016/B978-0-08-092493-9.50007-4 Google Scholar 4dC. R. Landis, J. Halpern, J. Am. Chem. Soc. 1987, 109, 1746–1754; 10.1021/ja00240a025 CASWeb of Science®Google Scholar 4eC. R. Landis, S. Feldgus, Angew. Chem. 2000, 112, 2985–2988; 10.1002/1521-3757(20000818)112:16 3.0.CO;2-P Google ScholarAngew. Chem. Int. Ed. 2000, 39, 2863–2866; 10.1002/1521-3773(20000818)39:16 3.0.CO;2-K CASPubMedWeb of Science®Google Scholar 4fS. Feldgus, C. R. Landis, J. Am. Chem. Soc. 2000, 122, 12 714–12 727. 10.1021/ja0019373 CASWeb of Science®Google Scholar 5D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159–1171; 10.1002/ange.19951071004 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 1059–1064. (“The goal of channeling the catalysis through one particular complex is usually achieved by an overwhelming kinetic activity favoring that one complex over the many other complexes which assemble in solution. For ligand-accelerated processes with early transition metal complexes, this in situ selection of a highly reactive (and selective) metallic complex from a variety of thermodynamically dictated assemblies is a crucial requirement.” 10.1002/anie.199510591 CASWeb of Science®Google Scholar 6 6aB. McCulloch, J. Halpern, M. R. Thomas, C. R. Landis, Organometallics 1990, 9, 1392–1395; 10.1021/om00119a006 CASWeb of Science®Google Scholar 6bH.-J. Drexler, S. Zhang, A. Sun, A. Spannenberg, A. Arrieta, A. Preetz, D. Heller, Tetrahedron: Asymmetry 2004, 15, 2139–2150. 10.1016/j.tetasy.2004.06.036 CASWeb of Science®Google Scholar 7D. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534–3543. 10.1021/ja012639o CASPubMedWeb of Science®Google Scholar 8M. Yasutake, I. D. Gridnev, N. Higashi, T. Imamoto, Org. Lett. 2001, 3, 1701–1704. 10.1021/ol0158967 CASPubMedWeb of Science®Google Scholar 9 9aD. Heller, H.-J. Drexler, J. You, W. Baumann, K. Drauz, H.-P. Krimmer, A. Börner, Chem. Eur. J. 2002, 8, 5196–5202; 10.1002/1521-3765(20021115)8:22 3.0.CO;2-P CASPubMedWeb of Science®Google Scholar 9bD. Heller, H.-J. Drexler, A. Spannenberg, B. Heller, J. You, W. Baumann, Angew. Chem. 2002, 114, 814–817; 10.1002/1521-3757(20020301)114:5 3.0.CO;2-J Google ScholarAngew. Chem. Int. Ed. 2002, 41, 777–780; 10.1002/1521-3773(20020301)41:5 3.0.CO;2-7 CASPubMedWeb of Science®Google Scholar 9cD. Heller, R. Thede, D. Haberland, J. Mol. Catal. A 1997, 115, 273–281. 10.1016/S1381-1169(96)00341-X CASWeb of Science®Google Scholar 10CCDC 216557, CCDC 216558, CCDC 247714, CCDC 247715, CCDC 247716, and CCDC-247717 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or [email protected]). Google Scholar 11W. D. Lubell, M. Kitamura, R. Noyori, Tetrahedron: Asymmetry 1991, 2, 543–554. 10.1016/S0957-4166(00)86107-8 CASGoogle Scholar 12A. Chiaroni, C. Riche, F. Dumas, D. Potin, J. D'Angelo, Acta Crystallogr. Sect. C 1995, 51, 967–970. 10.1107/S0108270193007383 Web of Science®Google Scholar 13 13aJ. A. Ramsden, T. D. W. Claridge, J. M. Brown, J. Chem. Soc. Chem. Commun. 1995, 2469–2471; 10.1039/C39950002469 CASWeb of Science®Google Scholar 13bT. Imamoto, H. Tsuruta, Y. Wada, H. Masuda, K. Yamaguchi, Tetrahedron Lett. 1995, 36, 8271–8274. 10.1016/0040-4039(95)01775-D CASWeb of Science®Google Scholar 14The chloro compound was chosen because the absolute configuration of the main hydrogenation product has been proven by X-ray structure analysis and therefore the assignment of the HPLC-Chiralyser signals is definite.[3b] Google Scholar 15[P]/[P*]=[major substrate complex]/[minor substrate complex] (kmaj/kmin); D. Heller, H. Buschmann, H.-D. Scharf, Angew. Chem. 1996, 108, 1964–1967; 10.1002/ange.19961081623 Google ScholarAngew. Chem. Int. Ed. 1996, 35, 1852–1854. An analogous equation with the stability constants resulting from the equilibrium treatment was already described by Halpern and Landis.[4d] For the equation used here resulting from the steady-state treatment, the ratio of the stability constants must be replaced by the reciprocal values of the corresponding Michaelis constants. 10.1002/anie.199618521 CASWeb of Science®Google Scholar 16These considerations apply only if the ratio of the diastereomeric substrate complexes determined under argon corresponds to that under hydrogen atmosphere. For the hydrogenation of methyl (Z)-N-acetylaminocinnamate with the dipamp catalyst this seems to be the case: D. Heller, H. Buschmann, Top. Catal. 1998, 5, 159–176. 10.1023/A:1019185532627 CASWeb of Science®Google Scholar 17For a detailed mechanistic study of the analogous hydrogenation with Ru catalysts, see: M. Kitamura, M. Tsukamoto, Y. Bessho, M. Yoshimura, U. Kobs, M. Widmalm, R. Noyori, J. Am. Chem. Soc. 2002, 124, 6649–6667. 10.1021/ja010982n CASPubMedWeb of Science®Google Scholar Citing Literature Volume44, Issue8February 11, 2005Pages 1184-1188 ReferencesRelatedInformation

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