Syntheses of new dimeric-Cinchona alkaloid as a chiral phase transfer catalysts for the alkylation of Schiff base

Journal of Molecular Catalysis A: Chemical

Volumn 241, Issue 1-2, 2005, Pages 111-117

  Siva, Ayyanar ^a   Murugan, Eagambaram ^b  

^a GANDHIGRAM RURAL UNIVERSITY   (India)

^b UNIVERSITY OF MADRAS   (India)

Author keywords

Cinchona alkaloid; Dimeric catalyst; Enantioselection; Phase transfer catalyst; Schiff base

Indexed keywords

ALKYLATION; CATALYSTS; ESTERS; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL);

CINCHONA ALKALOID; DIMERIC SELECTION; ENANTIOSELECTION; PHASE TRANSFER CATALYST; SCHIFF BASE;

AMMONIUM COMPOUNDS;

EID: 25844477525     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.06.059     Document Type: Article

References (53)

1. E.V. Dehmlow, and S.S. Dehmlow Phase Transfer Catalysis third ed. 1993 VCH Weinheim
2. C.M. Starks, C.L. Liotta, and M. Halpern Phase Transfer Catalysis - Fundamentals, Applications and Industrial Perspectives 1994 Chapman and Hall New York
3. M. Halpern Phase Transfer Catalysis Symposium Series, vol. 659 1995 American Chemical Society, ACS Washington, DC
4. M. Makosza, and B. Serafinowa Rocz. Chem. 39 1965 1223 1225
5. C.M. Starks J. Am. Chem. Soc. 93 1971 195 199
6. M.J. O'Donnell, W.D. Bennett, and S. Wu J. Am. Chem. Soc. 111 1989 2353 2355
7. M.J. O'Donnell I. Ojima Catalytic Asymmetric Synthesis 1993 VCH Publishers New York 389 (Chapter 8)
8. T. Shioiri Y. Sasson R. Neumann Handbook of Phase-Transfer Catalysis 1997 Blackie Academic & Professional London (Chapter 14)
9. D. Martyres Synlett 4 1999 1508
10. A. Nelson Angew. Chem. Int. Ed. 38 1999 1583 1585
11. T. Abellan, R. Chinechilla, N. Galindo, G. Guillena, C. Najera, and J.M. Sansano Eur. J. Org. Chem. 15 2000 2689 2697
12. M.J. O'Donnell I. Ojima Catalytic Asymmetric Synthesis 2000 VCH New York 389 411
13. M.J. O'Donnell Aldrichim. Acta 34 2001 3 13
14. K. Kacprzak, and J. Gawronski Synthesis 7 2001 961 998
15. E.J. Corey, and F.-Y. Zhang Org. Lett. 2 2000 4257 4259
16. T. Perrard, J.-C. Plaquevent, J.-R. Desmurs, and D. Hebrault Org. Lett. 2 2000 2959 2962
17. D.Y. Kim, S.C. Huh, and S.M. Kim Tetrahedron Lett. 42 2001 6299 6301
18. S. Arai, and T. Shioiri Tetrahedron 58 2002 1407 1413
19. R.C.D. Brown, and J.F. Keily Angew. Chem. Int. Ed. 40 2001 4496 4498
20. S. Arai, H. Tsuge, M. Oku, M. Miura, and T. Shioiri Tetrahedron 58 2002 1623 1630
21. B. Lygo, and C.M. To Tetrahedron Lett. 42 2001 1343 1346
22. M. Horikawa, J. Buch-Petersen, and E.J. Corey Tetrahedron Lett. 40 1999 3843 3846
23. T. Ooi, K. Doda, and K. Maruoka Org. Lett. 3 2001 1273 1276
24. E.J. Corey, and F.-Y. Zhang Angew. Chem. Int. Ed. 38 1999 1931 1934
25. D.Y. Kim, and E.J. Park Org. Lett. 4 2002 545 547
26. N. Shibata, E. Suzuki, and Y.J. Takeuchi Am. Chem. Soc. 122 2000 10728 10729
27. B. Mohar, J. Baudoux, J.-C. Plaquevent, and D. Cahard Angew. Chem. Int. Ed. 40 2001 4214 4216
28. T. Ooi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 121 1999 6519 6520
29. T. Ooi, E. Tayama, K. Doda, M. Takeuchi, and K. Maruoka Synlett 10 2000 1500 1502
30. T. Ooi, M. Takeuchi, M. Kameda, and K. Marouka J. Am. Chem. Soc. 122 2000 5228 5229
31. K. Manabe Tetrahedron Lett. 39 1998 5807 5810
32. K. Manabe Tetrahedron 54 1998 14456 14476
33. Y.-N. Belokon, K.A. Kotchetkov, T.D. Churloma, N.S. Ikonnikov, A.A. Chesnokov, A.V. Larionov, V.S. Parmar, R. Kumar, and H.B. Kagan Tetrahedron: Asymmetry 9 1998 851 857
34. Y.N. Belokon', K.A. Kotchetkov, T.D. Churkina, N.S. Ikonnikov, A.A. Chesnokov, A.V. Larionov, I. Sing, V.S. Parmer, S. Vyskocil, and H.B. Kagan J. Org. Chem. 65 2000 7041 7048
35. Y.N. Belokon', K.A. Kotchetkov, T.D. Churkina, N.S. Ikonnikov, S. Vyskocil, and H.B. Kagan Tetrahedron: Asymmetry 10 1999 1723 1728
36. Y.N. Belokon', K.A. Kotchetkov, T.D. Churkina, N.S. Ikonnikov, O.V. Larionov, S.R. Harutyunyan, S. Vyskocil, M. North, and H.B. Kagan Angew. Chem. Int. Ed. 40 2001 1948 1951
37. J. Casas, C. Najera, J.M. Sansano, J. Gonzalez, J.M. Saa, and M. Vega Tetrahedron: Asymmetry 12 2001 699 702
38. Y.N. Belokon', M. North, V.S. Kublitski, N.S. IkonNikov, P.E. Krasik, and V.L. Maleev Tetrahedron Lett. 40 1999 6105 6108
39. Y.N. Belokon, R.G. Davies, and M. North Tetrahedron Lett. 41 2000 7245 7248
40. U.H. Dolling, P. Davis, and E.J. Grabowski J. Am. Chem. Soc. 106 1984 446 447
41. K. Soai, and M. Watanabe Chem. Commun. 1 1990 43 44
42. D.J. Cram, and G.D.Y. Sogah Chem. Commun. 13 1981 625 626
43. M. Masui, A. Ando, and T. Shioiri Tetrahedron Lett. 29 1988 2835 2838
44. B. Lygo, and P.G. Wainwright Tetrahedron Lett. 38 49 1997 8595 8598
45. E.J. Corey, F. Xu, and M.C. Noe J. Am. Chem. Soc. 119 1997 12414
46. E.J. Corey, F. Xu, and M.C. Noe Tetrahedron Lett. 39 1998 5347
47. S. Jew, B. Jeong, M. Yoo, H. Huh, and H. Park Chem. Commun. 14 2001 1244 1245
48. H. Park, B. Jeong, M. Yoo, H. Huh, M. Park, and S. Jew Tetrahedron Lett. 42 2001 4645 4648
49. Z. Zhang, Y. Wang, W. Zhen, and P. Hodge React. Funct. Polym. 41 1999 37 43
50. R. Chinchilla, P. Mazon, and C. Nagera Tetrahedron: Asymmetry 11 2000 3277 3281
51. N.M. Alococ, P. Moore, and K.F. Mok J. Chem. Soc. Perkin II 7 1979 1186 1190
52. E.J. Corey, F. Xu, and M.C. Noe J. Am. Chem. Soc. 119 1997 12414 12416
53. K. Maruoka, and T. Ooi Chem. Rev. 103 2003 3013 3028