SimplePhos Monodentate Ligands: Synthesis and Application in Copper-Catalyzed Reactions
Eine einfache Wahl: Die Liganden L* mit chiralen Amino‐ und flexiblen Arylgruppen am Phosphoratom erhielten den Namen „SimplePhos“. Sie bewirken eine hoch enantioselektive kupferkatalysierte konjugierte Addition und allylische Substitution mit Dialkylzink‐ und Trialkylaluminiumreagentien (siehe Sche...
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| Published in | Angewandte Chemie Vol. 119; no. 39; pp. 7606 - 7609 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.10.2007
WILEY‐VCH Verlag |
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| Abstract | Eine einfache Wahl: Die Liganden L* mit chiralen Amino‐ und flexiblen Arylgruppen am Phosphoratom erhielten den Namen „SimplePhos“. Sie bewirken eine hoch enantioselektive kupferkatalysierte konjugierte Addition und allylische Substitution mit Dialkylzink‐ und Trialkylaluminiumreagentien (siehe Schema; CuTC=Kupferthiophencarboxylat). |
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| AbstractList | Eine einfache Wahl: Die Liganden L* mit chiralen Amino‐ und flexiblen Arylgruppen am Phosphoratom erhielten den Namen „SimplePhos“. Sie bewirken eine hoch enantioselektive kupferkatalysierte konjugierte Addition und allylische Substitution mit Dialkylzink‐ und Trialkylaluminiumreagentien (siehe Schema; CuTC=Kupferthiophencarboxylat). |
| Author | Alexakis, Alexandre Bernardinelli, Gérald Vuagnoux-d'Augustin, Magali Palais, Laëtitia Mikhel, Igor S. Bournaud, Chloée Micouin, Laurent Falciola, Caroline A. Rosset, Stéphane |
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| Notes | Swiss National Research Foundation - No. 200020-113332 The authors thank the Swiss National Research Foundation (grant no. 200020-113332) for financial support, and BASF for a generous gift of chiral amines. ark:/67375/WNG-F456D41Q-9 ArticleID:ANGE200702186 istex:D4BC1EA44F99953D72CD3391FE179015B7F0522E The authors thank the Swiss National Research Foundation (grant no. 200020‐113332) for financial support, and BASF for a generous gift of chiral amines. |
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| References | A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen, C. Benhaim, Synlett 2001, 1375-1378 A. Alexakis, D. Polet, S. Rosset, S. March, J. Org. Chem. 2004, 69, 5660-5667 N. Krause, A. Hoffmann-Röder, Synthesis 2001, 7, 171-196 A. Alexakis, C. Malan, L. Lea, K. Tissot-Croset, D. Polet, C. Falciola, Chimia 2006, 60, 124-130 L. Micouin, A. Alexakis, C. Bournaud, C. Falciola, T. Lecourt, S. Rosset, Org. Lett. 2006, 8, 3581-3584. See also M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061. B. L. Feringa, M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, J. Am. Chem. Soc. 2000, 122, 11539-11540. A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3223 K. Mikami, K. Aikawa, Y. Yusa, J. J. Jodry, M. Yamanaka, Synlett 2002, 1561-1578. S. Jugé, C. Darcel, E. B. Kaloum, R. Merdès, D. Moulin, N. Riegel, S. Thorimbert, J. P. Genêt, J. Organomet. Chem. 2001, 624, 333-343. Angew. Chem. Int. Ed. 2005, 44, 4435-4439. B. L. Feringa, J.-G. Boiteau, R. Imbos, A. J. Minnaard, Org. Lett. 2003, 5, 681-684 S. Jugé, N. Riegel, C. Darcel, O. Stephan, J. Organomet. Chem. 1998, 567, 219-223 Angew. Chem. Int. Ed. 2005, 44, 1376-1378. A. Alexakis, C. A. Falciola, Angew. Chem. 2007, 119, 2673-2676 B. L. Feringa, Acc. Chem. Res. 2000, 33, 346-353 A. Alexakis, M. d'Augustin, L. Palais, Angew. Chem. 2005, 117, 1400-1402 M. Pineschi, F. Del Moro, P. Crotti, F. Macchia, Org. Lett. 2005, 7, 3605-3609. Angew. Chem. Int. Ed. 2007, 46, 2619-2622. A. Alexakis, D. Polet, C. Benhaim, S. Rosset, Tetrahedron: Asymmetry 2004, 15, 2199-2203. H. Yorimitsu, K. Oshima, Angew. Chem. 2005, 117, 4509-4513 2006; 60 2001; 7 2001 2000; 56 2004; 69 2000; 33 2004; 15 2006; 8 2005; 7 2003; 5 2000; 122 2002 1998; 567 2007 2007; 119 46 2001; 624 2005 2005; 117 44 |
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| Snippet | Eine einfache Wahl: Die Liganden L* mit chiralen Amino‐ und flexiblen Arylgruppen am Phosphoratom erhielten den Namen „SimplePhos“. Sie bewirken eine hoch... |
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| SubjectTerms | Asymmetrische Katalyse Enone Konjugierte Additionen Kupfer P-Liganden |
| Title | SimplePhos Monodentate Ligands: Synthesis and Application in Copper-Catalyzed Reactions |
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