Cinchona-Derived Chiral Poly(Phase-Transfer Catalysts) for Asymmetric Synthesis

Asymmetric Phase Transfer Catalysis

Volumn , Issue , 2008, Pages 49-70

  Jew, Sang sup ^a   Park, Hyeung geun ^a  

^a Seoul National University   (South Korea)

Author keywords

Chiral poly(phase transfer catalysts); Cinchona alkaloids; Dimeric ammonium salts; Dimeric cinchona phase transfer catalysts

Indexed keywords

EID: 59349121181     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527622627.ch4     Document Type: Chapter

References (68)

1. For excellent reviews, see: O'Donnell, M.J. (2000) in Catalytic Asymmetric Synthesis, 2nd edn. (ed. I. Ojima), Wiley-VCH, Weinheim, Chapter 10;
2. Nelson, A. (1999) Angew. Chem., Int. Ed., 38, 1583-1585;
3. Shioiri, T. and Arai, S. (2000) in Stimulating Concepts in Chemistry 2nd edn (eds F. Vögtle, J.F. Stoddart and M. Shibasaki), John Wiley & Sons, New York, pp. 123-143;
4. Kacprzak, K. and Gawronski, J. (2001) Synthesis, 961-998;
5. Taggi, A.E., Hafez, A.M. and Lectka, T. (2003) Acc. Chem. Res., 36, 10-19;
6. Tian, S.-K., Chen, Y., Hang, J., Tang, L., McDaid, P. and Deng, L. (2004) Acc. Chem. Res., 37, 621-631.
7. O'Donnell, M.J. (2001) Aldrichimica Acta, 34, 3-15;
8. O'Donnell, M.J. (2004) Acc. Chem. Res., 37, 506-517, and references cited therein.
9. Corey, E.J., Bo, Y. and Busch-Petersen, J. (1998) J. Am. Chem. Soc., 120, 13000-13001.
10. Hermann, K. and Wynberg, H. (1979) J. Org. Chem., 44, 2238-2244;
11. Conn, R.S.E., Lovell, A.V., Karady, S. and Weinstock, L.M. (1986) J. Org. Chem., 51, 4710-4711;
12. Zhang, F.-Y. and Corey, E.J. (2000) Org. Lett., 2, 1097-1100;
13. Zhang, F.-Y. and Corey, E.J. (2001) Org. Lett., 3, 639-641;
14. Corey, E.J., Noe, M.C. and Xu, F. (1998) Tetrahedron Lett., 39, 5347-5350;
15. Perrard, T., Plaquevent, J.-C., Desmurs, J.-R. and Hébrault, D. (2000) Org. Lett., 2, 2959-2962;
16. Colonna, S., Hiemstra, H. and Wynberg, H. (1978) J. Chem. Soc. Chem. Commun., 238-239;
17. Corey, E.J. and Zhang, F.-Y. (2000) Org. Lett., 2, 4257-4259.
18. Ando, A., Miura, T., Tatematsu, T. and Shioiri, T. (1993) Tetrahedron Lett., 34, 1507-1510;
19. Shioiri, T., Bohsako, A. and Ando, A. (1996) Heterocycles, 42, 93-97;
20. Gasparski, C.M. and Miller, M.J. (1991) Tetrahedron, 47, 5367-5378;
21. Horikawa, M., Busch-Peteren, J. and Corey, E.J. (1999) Tetrahedron Lett., 40, 3843-3846;
22. Ando, A., Miura, T., Tatematsu, T. and Shioiri, T. (1993) Tetrahedron Lett., 34, 1507-1510.
23. Hummelen, J.C. and Wynberg, H. (1978) Tetrahedron Lett., 19, 1089-1092;
24. Arai, S. and Shioiri, T. (1998) Tetrahedron Lett., 39, 2145-2148;
25. Arai, S., Shirai, Y., Ishida, T. and Shioiri, T. (1999) J. Chem. Soc. Chem. Commun., 49-50;
26. Arai, S., Shirai, Y., Ishida, T. and Shioiri, T. (1999) Tetrahedron, 55, 6375-6386;
27. Arai, S., Ishida, T. and Shioiri, T. (1998) Tetrahedron Lett., 39, 8299-8302;
28. Arai, S. and Shioiri, T. (2002) Tetrahedron, 58, 1407-1413.
29. Helder, R., Hummelen, J.C., Laane, R.W.P.M., Wiering, J.S. and Wynberg, H. (1976) Tetrahedron Lett., 17, 1831-1834;
30. Hummelen, J.C. and Wynberg, H. (1978) Tetrahedron Lett., 19, 1089-1092;
31. Wynberg, H. and Greijdanus, B. (1978) J. Chem. Soc. Chem. Commun., 427-428;
32. Pluim, H. and Wynberg, H. (1980) J. Org. Chem., 45, 2498-2502;
33. Wynberg, H. and Marsman, B. (1980) J. Org. Chem., 45, 158-161;
34. Harigaya, Y., Yamaguchi, H. and Onda, M. (1981) Heterocycles, 15, 183-185;
35. Baba, N., Oda, J. and Kawaguchi, M. (1986) Agric. Biol. Chem., 50, 3113-3117;
36. MacDonald, G., Alcaraz, L., Lewis, N.J. and Taylor, R.J.K. (1998) Tetrahedron Lett., 39, 5433-5436;
37. Alcaraz, L., MacDonald, G., Ragot, J.P., Lewis, N. and Taylor, R.J.K. (1998) J. Org. Chem., 63, 3526-3527;
38. Barrett, A.G.M., Blaney, F., Campbell, A.D., Hamprecht, D., Meyer, T., White, A.J.P., Witty, D. and Williams, D.J. (2002) J. Org. Chem., 67, 2735-2750;
39. Adam, W., Rao, P.B., Degen, H.-G. and Saha-Möller, C.R. (2001) Tetrahedron: Asymmetry, 12, 121-125;
40. Adam, W., Rao, P.B., Degen, H.-G., Levai, A., Patonay, T. and Saha-Möller, C.R. (2001) J. Org. Chem., 67, 259-264;
41. Lygo, B. and To, D.C.M. (2001) Tetrahedron Lett., 42, 1343-1346;
42. Lygo, B. and Wainwright, P.G. (1999) Tetrahedron Lett., 39, 1599-1602;
43. Lygo, B. and Wainwright, P.G. (1999) Tetrahedron, 55, 6289-6300;
44. Corey, E.J. and Zhang, F.-Y. (1999) Org. Lett., 1, 1287-1290;
45. Arai, S., Tsuge, H. and Shioiri, T. (1998) Tetrahedron Lett., 39, 7563-7566;
46. Arai, S., Oku, M., Miura, M. and Shioiri, T. (1998) Synlett, 1201-1202;
47. Arai, S., Tsuge, H., Oku, M., Miura, M. and Shioiri, T. (2002) Tetrahedron, 58, 1623-1630.
48. Jew, S.-S., Jeong, B.-S., Yoo, M.-S., Huh, H. and Park, H.-G. (2001) Chem. Commun., 1244-1245.
49. Sharpless, K.B., Amberg, W., Bennani, Y.L., Crispino, G.A., Hartung, J., Jeong, K.-S., Kwong, H.-L., Morikawa, K., Wang, Z.-M., Xu, D. and Zhang, X.-L. (1992) J. Org. Chem., 57, 2768-2771;
50. Amberg, W., Bennani, Y.L., Chadha, R.K., Crispino, G.A., David, W.D., Hartung, J., Jeong, K.-S., Ogino, Y., Shibata, T. and Sharpless, K.B. (1993) J. Org. Chem., 58, 844-849;
51. Crispino, G.A., Jeong, K.-S., Kolb, H.C., Wang, Z.-M., Xu, D. and Sharpless, K.B. (1993) J. Org. Chem., 58, 3785-3786;
52. Lee, J.-H., Yoo, M.-S., Jew, S.-S., Park, H.-G. and Jeong, B.-S. (2007) Tetrahedron, 63, 7906-7915.
53. Park, H.-G., Jeong, B.-S., Yoo, M.-S., Lee, J.-H., Park, B.-S., Kim, M.G. and Jew, S.-S. (2003) Tetrahedron Lett., 44, 3497-3500.
54. Jew, S.-S., Yoo, M.-S., Jeong, B.-S., Park, I.Y. and Park, H.-G. (2002) Org. Lett., 4, 4245-4248;
55. Yoo, M.-S., Jeong, B.-S., Lee, J.-H., Park, H.-G. and Jew, S.-S. (2005) Org. Lett., 7, 1129-1131.
56. Park, H.-G., Jeong, B.-S., Yoo, M.-S., Lee, J.-H., Park, M.-K., Lee, Y.-J., Kim, M.-J. and Jew, S.-S. (2002) Angew. Chem., Int. Ed., 41, 3036-3038.
57. Park, H.-G., Jeong, B.-S., Yoo, M.-S., Park, M.-K., Huh, H. and Jew, S.-S. (2001) Tetrahedron Lett., 42, 4645-4648.
58. Lygo, B. and Wainwright, P.G. (1997) Tetrahedron Lett., 38, 8595-8598;
59. Corey, E.J., Xu, F. and Noe, M.C. (1997) J. Am. Chem. Soc., 119, 12414-12415.
60. Chinchilla, R., Mazón, P. and Nájera, C. (2002) Tetrahedron: Asymmetry, 13, 927-931.
61. Chinchilla, R., Mazón, P., Nájera, C. and Ortega, F.J. (2004) Tetrahedron: Asymmetry, 15, 2603-2607.
62. Chinchilla, R., Mazón, P., Nájera, C., Ortega, F.J. and Yus, M. (2005) Arkivoc, 222-232.
63. Siva, A. and Murugan, E. (2005) J. Mol. Catal. A.: Chem., 241, 111.
64. Siva, A. and Murugan, E. (2005) Synthesis, 2927-2933;
65. Siva, A. and Murugan, E. (2006) J. Mol. Catal. A.:Chem., 248, 1-9.
66. Wang, X., Yin, L., Yang, T. and Wang, Y. (2007) Tetrahedron: Asymmetry, 18, 108-114.
67. Jew, S.-S., Lee, J.-H., Jeong, B.-S., Yoo, M.-S., Kim, M.-J., Lee, Y.-J., Lee, J., Choi, S.-H., Lee, K., Lah, M.S. and Park, H.-G. (2005) Angew. Chem., Int. Ed., 44, 1383-1385.
68. Lv, J., Wang, X., Liu, J., Zhang, L. and Wang, Y. (2006) Tetrahedron: Asymmetry, 17, 330-335.