Highly enantioselective nitroaldol reactions catalyzed by copper(II) complexes derived from substituted 2-(pyridin-2-yl)imidazolidin-4-one ligands

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4787-4793

  Panov, Illia ^a   Drabina, Pavel ^a   Padělková, Zdeňka ^a   Šimůnek, Petr ^a   Sedlák, Miloš ^a  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; COPPER COMPLEXES; CU COMPLEXES; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSTS; NITROALDOL; NITROMETHANE;

ALDEHYDES; COPPER COMPOUNDS;

LIGANDS;

COPPER COMPLEX; IMIDAZOLIDINE DERIVATIVE; LIGAND;

ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 79957810720     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200703j     Document Type: Article

References (30)

1. Seebach, D.; Beck, A. K.; Mukhopadhyay., T.; Thomas, E. Helv. Chim. Acta 1982, 63, 1101-1133
2. Corey, E. J.; Zhang, F. U. Angew. Chem., Int. Ed. 1999, 38, 1931-1933
3. Luzio, F. A. Tetrahedron 2001, 57, 915-945
4. Palomo, C.; Oiarbide, M.; Laso, A. Angew. Chem., Int. Ed. 2005, 44, 3881-3884
5. Boruwa, J.; Naminita Gogoi, N.; Saikia, P. P.; Barua, N. C. Tetrahedron: Asymmetry 2006, 57, 3315-3326
6. Kwong, H.-L.; Yeung, H.-L.; Yeung, C.-T.; Lee, W.-S.; Lee, C.-S.; Wong, W.-L. Coord. Chem. Rev. 2007, 251, 2188-2222
7. Arai, T.; Takashita, R.; Endo, Y.; Watanabe, M.; Yanagisawa, A. J. Org. Chem. 2008, 73, 4903-4906
8. Constable, E. C.; Zhang, G.; Housecroft, C. E.; Neuburger, M.; Schaffner, S.; Woggon, W.-D.; Zampese, J. A. New J. Chem. 2009, 33, 2166-2173
9. Spangler, K. Y.; Wolf, C. Org. Lett. 2009, 11, 4724-4727
10. Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692-12693
11. Sedlák, M.; Drabina, P.; Keder, R.; Hanusek, J.; Císařová, I.; Růžička, A. J. Organomet. Chem. 2006, 691, 2623-2630
12. Keder, R.; Drabina, P.; Hanusek, J.; Sedlák, M. Chem. Pap. 2006, 60, 324-326
13. Ma, K.; You, J. Chem. Eur. J. 2007, 13, 1863-1871
14. Blay, G.; Domingo, L. R.; Hernández V.; Pedro, J. R. Chem. Eur. J. 2008, 14, 4725-4730
15. Constable, E. C.; Zhang, G.; Housecroft, C. E.; Neuburger, M.; Schaffner, S.; Woggon, W.-D. New J. Chem. 2009, 33, 1064-1069
16. Arai, T.; Suzuki, K. Synlett 2009, 3167-3170
17. Jones, M. D.; Cooper, C. J.; Mahon, M. F.; Raithby, P. R.; Apperley, D.; Wolowska, J.; Collison, D. J. Mol. Catal. A 2010, 325, 8-14
18. Noole, A.; Lippur, K; Metsala, A.; Loop, M.; Kanger, T. J. Org. Chem. 2010, 75, 1313-1316
19. Panov, I.; Drabina, P.; Padělková, Z.; Hanusek, J.; Sedlák, M. J. Heterocycl. Chem. 2010, 47, 1356-1360
20. Lelais, G.; MacMillan, D. W. C. Aldrichim. Acta 2006, 39, 79-87
21. Wepplo, P. J. Pestic. Sci. 1990, 29, 293-315
22. Harris, J. E.; Gagne, J. A.; Fischer, J. E.; Sharma, R. R.; Traul, K. A.; Scot, J. D.; Hess, F. G. In The Imidazole Herbicides; Shaner, D. L.; OConnor, S. L., Eds.; CRC Press: Boca Raton, FL, 1991.
23. Drabina, P.; Sedlák, M.; Růžička, A.; Malkov, A.; Kočovský, P. Tetrahedron: Asymmetry 2008, 19, 384-390
24. Claridge, T. D. W.; In High-Resolution NMR Techniques in Organic Chemistry; Pergamon: Amsterdam, 1999; p 320.
25. Wernerova, M.; Hudlický, T. Synlett 2010, 2701-2707
26. Hartley, F. R. Chem. Soc. Rev. 1973, 2, 163-179
27. Panov, I.; Drabina, P.; Hanusek, J.; Sedlák, M. Tetrahedron: Asymmetry 2011, 22, 215-211
28. Rewell, J. D.; Wennemers, H Adv. Synth. Catal. 2008, 350, 1046-1052
29. Veverková, E.; Štrasserová, J.; Šebesta, R.; Toma, Š. Tetrahedron: Asymmetry 2010, 21, 58-61
30. Hut'ka, M.; Poláčková, V.; Marák, J.; Kaniansky, D.; Šebesta, R.; Toma, Š. Eur. J. Org. Chem. 2010, 6430-6435