New chiral imidazolinic derivatives

Tetrahedron Asymmetry

Volumn 16, Issue 5, 2005, Pages 1017-1023

  Génisson, Yves ^a   Lauth De Viguerie, Nancy ^b   André, Chantal ^a   Baltas, Michel ^a   Gorrichon, Liliane ^a  

^a UPS)   (France)

^b Université Paul Sabatier   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; IMIDAZOLE DERIVATIVE; IMIDAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS; ROOM TEMPERATURE; X RAY DIFFRACTION;

EID: 14344253308     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.01.014     Document Type: Article

References (32)

1. Y. Génisson, C. Marazano, M. Mehmandoust, D. Gnecco, and B.C. Das Synlett 5 1992 431 434
2. B. Guilloteau-Bertin, D. Compere, L. Gil, C. Marazano, and B.C. Das Eur. J. Org. Chem. 8 2000 1391 1399 and references cited therein
3. Review on ionic liquid and chirality: C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, and J.-C. Plaquevent Tetrahedron: Asymmetry 14 2003 3081 3093
4. C.E. Song Chem. Commun. 2004 1033 1043
5. Significant examples of chiral ionic liquids: M.J. Earle, P.B. McCormac, and K.R. Seddon Green Chem. 1 1999 23 25
6. P. Wasserscheid, A. Bösmann, and C. Bolm Chem. Commun. 2002 200 201
7. J. Levillain, G. Dubant, I. Abrunhosa, M. Gulea, and A.-C. Gaumont Chem. Commun. 2003 2914 2915
8. C. Pastrascu, C. Sugisaki, C. Mingotaud, J.-D. Marty, Y. Génisson, and N. Lauth-de Viguerie Heterocycles 63 2004 2033 2041
9. W. Bao, Z. Wang, and Y. Li J. Org. Chem. 68 2003 591 593
10. J.J. Jodry, and K. Mikami Tetrahedron Lett. 45 2004 4429 4431
11. Other RTILs based on a chiral imidazolium core: J. Horwath, K. Hanlon, D. Fayne, and P. McCormac Tetrahedron Lett. 38 1997 3097 3100
12. Y. Ishida, H. Miyauchi, and K. Saigo Chem. Commun. 2002 2240 2241
13. N.M.T. Lourenço, and C.A.M. Afonso Tetrahedron 59 2003 789 794
14. R.T. Dere, R.R. Pal, P.S. Patil, and M.M. Salunkhe Tetrahedron Lett. 44 2003 5351 5353
15. The use of a water/RTIL biphasic system have also been shown to promote conjugate addition of thiols to enones: J.S. Yadav, B.V.S. Reddy, and G. Baishya J. Org. Chem. 68 2003 7098 7100
16. B. Wang, Y.-R. Kang, L.-M. Yang, and J.-S. Suo J. Mol. Cat. A 203 2003 29 36
17. Review on asymmetric nucleophilic catalyst with chiral amines: S. France, D.J. Guerin, S.J. Miller, and T. Lectka Chem. Rev. 103 2003 2985 3012
18. U. Gruseck, and M. Heuschmann Chem. Ber. 120 1987 2053 2064
19. For a related examples of non C-2 substituted chiral imidazole see: J. Liu, J. Chen, J. Zhao, Y. Zhao, L. Li, and H. Zhang Synthesis 17 2003 2661 2666
20. D.E. Frantz, L. Morency, A. Soheili, J.A. Murry, E.J.J. Grabowski, and R.D. Tillyer Org. Lett. 6 2004 843 846
21. T. Prisinzano, H. Law, M. Dukat, A. Slassi, N. MaClean, L. Demchyshyn, and R.A. Glennon Bioorg. Med. Chem. 9 2001 613 619
22. A. Barco, S. Benetti, and G.P. Pollini Synthesis 1977 837
23. J.L. Hughey IV, S. Knapp, and H. Schugar Synthesis 1980 489 490
24. P.K. Kadaba Synthesis 1978 694 695
25. 20 Crystallographic data (excluding structure factors) for the structure reported herein have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. 240725 for ent-4b. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB1 1EZ, UK [Fax: (internat.) +44-1223/336-033; e-mail: deposit@ccdc.cam.ac.uk
26. G.M. Sheldrick Acta Crystallogr. A46 1990 467 473
27. Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Refinement; University of Gottingen, 1997
28. H.D. Flack Acta Crystallogr. A39 1983 876 881
29. For general trends concerning relationships between the structure of RTIL and their physicochemical properties see: J.L. Anthony, J.F. Brennecke, J.D. Holbrey, E.J. Maginn, R.A. Mantz, R.D. Rogers, P.C. Trulove, A.E. Visser, and T. Welton P. Wasserscheid T. Welton Ionic Liquids in Synthesis 2002 Wiley-VCH 41 126
30. See also: J. Dupont J. Braz. Chem. Soc. 15 2004 341 350
31. In the absence of the imidazolium 5 and under otherwise identical conditions, the Michael adduct was isolated in only 10% yield
32. H. Firouzabadi, and E. Ghaderi Tetrahedron Lett. 9 1978 839 840