New trimeric Cinchona alkaloid-based quaternary ammonium salts as efficient chiral phase transfer catalysts for enantioselective synthesis of α-amino acids

Journal of Molecular Catalysis A: Chemical

Volumn 248, Issue 1-2, 2006, Pages 1-9

  Siva, Ayyanar ^a   Murugan, Eagambaram ^b  

^a GANDHIGRAM RURAL UNIVERSITY   (India)

^b UNIVERSITY OF MADRAS   (India)

Author keywords

Amino acids; Cinchona alkaloid; Electrostatic force; Enantioselection; Ion pair interaction

Indexed keywords

ALKALINITY; AMINES; AMINO ACIDS; ESTERS; PHASE TRANSITIONS;

Α-AMINO ACIDS; CINCHONA ALKALOID; ENANTIOSELECTION; ION PAIR INTERACTION;

AMMONIUM COMPOUNDS;

EID: 33645406970     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.11.039     Document Type: Article

References (38)

1. T. Wirth Angew. Chem. Int. Ed. 35 1996 2708
2. M.J. O'Donnell, W.D. Bennett, and S. Wu J. Am. Chem. Soc. 111 1989 2353
3. E.J. Corey, F. Xu, and M.C. Noe J. Am. Chem. Soc. 119 1997 12414
4. E.J. Corey, M.C. Noe, and F. Xu Tetrahedron Lett. 39 1998 5347
5. E.J. Corey, Y. Bo, and J. Busch-Peterson J. Am. Chem. Soc. 120 1998 13000
6. B. Lygo, and P.G. Wainwright Tetrahedron Lett. 38 1997 8595
7. B. Lygo, J. Crosby, and J.A. Peterson Tetrahedron Lett. 40 1999 1389
8. B. Lygo Tetrahedron Lett. 40 1999 1389
9. B. Lygo, J. Crosby, and J.A. Peterson Tetrahedron Lett. 40 1999 8671
10. T. Ooi, E. Tayama, K. Doda, M. Takeuchi, and K. Maruoka Synlett 2000 1500
11. T. Ooi, M. Takeuchi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 122 2000 5228
12. D.A. Oare, and C.H. Heathcock Top. Stereochem. 19 1989 242
13. S. Kaneko, T. Yoshino, T. Katoh, and S. Terashima Heterocycles 46 1997 27
14. S. Kaneko, T. Yoshino, T. Katoh, and S. Terashima Tetrahedron 54 1998 5471
15. S. Arai, T. Ishida, and T. Shioiri Tetrahedron Lett. 39 1998 8299
16. B. Lygo, and P.G. Wainwright Tetrahedron Lett. 39 1998 1599
17. E.J. Corey, and F.-Y. Zhang Org. Lett. 1 1999 1287
18. S. Arai, H. Tsuge, and T. Shioiri Tetrahedron Lett. 39 1998 7563
19. T. Shioiri, A. Bohsako, and A. Ando Heterocycles 42 1996 93
20. E.J. Corey, and F.-Y. Zhang Angew. Chem. Int. Ed. 38 1999 1931
21. T. Ooi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 121 1999 6519
22. T. Ooi, E. Tayama, K. Doda, M. Takeuchi, and K. Maruoka Synlett 2000 1500
23. T. Ooi, M. Takeuchi, M. Kameda, and K. Marouka J. Am. Chem. Soc. 122 2000 5228
24. K. Manabe Tetrahedron Lett. 39 1998 5807
25. K. Manabe Tetrahedron 54 1998 14456
26. 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: Asymmetr. 9 1998 851
27. 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
28. Y.N. Belokon', K.A. Kotchetkov, T.D. Churkina, N.S. Ikonnikov, S. Vyskocil, and H.B. Kagan Tetrahedron: Asymmetr. 10 1999 1723
29. 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
30. J. Casas, C. Najera, J.M. Sansano, J. Gonzalez, J.M. Saa, and M. Vega Tetrahedron: Asymmetr. 12 2001 699 702
31. Y.N. Belokon', M. North, V.S. Kublitski, N.S. Ikon Nikov, P.E. Krasik, and V.L. Maleev Tetrahedron Lett. 40 1999 6105
32. Y.N. Belokon, R.G. Davies, and M. North Tetrahedron Lett. 41 2000 7245
33. S. Jew, B. Jeong, M. Yoo, H. Park, and H. Huh Chem. Commun. 2001 1244
34. H. Park, B. Jeong, M. Yoo, M. Park, H. Huh, and S. Jew Tetrahedron Lett. 42 2001 4645
35. H. Park, B. Jeong, M. Yoo, M. Park, H. Huh, J. Lee, Y. Lee, M. Kim, and S. Jew Angew. Chem. Int. Ed. 41 16 2002 3036
36. R. Chinchilla, P. Mazon, and C. Najera Tetrahedron: Asymmetr. 13 2002 927
37. S. Arai, M. Oku, T. Ishida, and T. Shioiri Tetrahedron Lett. 40 1999 6785
38. M.J. O'Donnell, S. Wu, and J.C. Huffman Tetrahedron 50 1994 4507