Cinchona-Mediated Enantioselective Protonations

Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis

Volumn , Issue , 2009, Pages 171-196

  Rouden, Jacques ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

Cinchona alkaloids; Decarboxylative protonation; Enantioselective protonation; Enolates; Enols; Ketenes; Michael additions; Proton migration

Indexed keywords

EID: 84890978682     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527628179.ch7     Document Type: Chapter

References (75)

1. Fehr, C. (1996) Angew. Chem. Int. Ed. Engl., 35, 2566-2587;
2. Eames, J. and Weerasooriya, N. (2001) Tetrahedron: Asymmetry, 12, 1-24;
3. Duhamel, L., Duhamel, P., and Plaquevent, J.-C. (2004) Tetrahedron: Asymmetry, 15, 3653-3691.
4. For a complete discussion on the chiral protonating agents, their structural and acidity requirements, see Duhamel, L., Duhamel, P., and Plaquevent, J.-C. (2004) Tetrahedron: Asymmetry, 15, 3653-3691.
5. Duhamel, L. (1976) C. R. Acad. Sci., 282, 125-127.
6. Takeuchi, S., Miyoshi, N., Hirata, K., Hayashida, H., and Ohga, Y. (1992) Bull. Chem. Soc. Jpn., 65, 2001-2003.
7. Poisson, T., Dalla, V., Marsais, F., Dupas, G., Oudeyer, S., and Levacher, V. (2007) Angew. Chem. Int. Ed., 46, 7090-7093.
8. Poisson, T., Oudeyer, S., Dalla, V., Marsais, F., and Levacher, V. (2008) Synlett, 2447-2450.
9. For the most recent examples of catalytic enantioselective protonations, see Cheon, C.H. and Yammamoto, H., (2008) J. Am. Chem. Soc., 130, 9246-9247;
10. Mitsuhashi, K., Ito, R., Arai, T., and Yanagisawa, A. (2006) Org. Lett., 8, 1721-1724;
11. Yanagisawa, A., Touge, T., and Arai, T. (2005) Angew Chem. Int. Ed., 44, 1546-1548;
12. Reynolds, N.T. and Rovis, T. (2005) J. Am. Chem. Soc., 127, 16406-16407.
13. Pracejus, H. (1960) Liebigs Ann. Chem., 634, 9-22;
14. Pracejus, H. and Tille, A. (1963) Chem. Ber., 96, 854-865;
15. Tille, A. and Pracejus, H. (1967) Chem. Ber., 100, 196-210;
16. Pracejus, H. and Kohl, G. (1969) Liebigs Ann. Chem., 722, 1-11.
17. Yamashita, T., Yasueda, H., Miyauchi, Y., and Nakamura, N. (1977) Bull. Chem. Soc. Jpn., 50, 1532-1534;
18. Yamashita, T., Yasueda, H., Nakatani, N., and Nakamura, N. (1978) Bull. Chem. Soc. Jpn., 51, 1183-1185;
19. Yamashita, T., Yasueda, H., and Nakamura, N. (1979) Bull. Chem. Soc. Jpn., 52, 2165-2166.
20. Blake, A.J., Friend, C.L., Outram, R.J., Simpkins, N.S., and Whitehead, A.J. (2001) Tetrahedron Lett., 42, 2877-2881.
21. Pracejus, H. (1960) Liebigs Ann. Chem., 634, 23-29.
22. Calmes, M., Escale, F., Glot, C., Rolland, M., and Martinez, J. (2000) Eur. J. Org. Chem., 2459-2466;
23. Calmes, M., Escale, F., and Martinez, J. (2002) Tetrahedron: Asymmetry, 13, 293-296.
24. For leading recent publications, see Fehr, C., (2007) Angew Chem. Int. Ed., 46, 7119-7121;
25. Schaefer, C. and Fu, G.C. (2005) Angew. Chem. Int. Ed., 44, 4606-4608;
26. Wiskur, S.L. and Fu, G.C. (2005) J. Am. Chem. Soc., 127, 6176-6177.
27. For recent examples, see Hayashi, T., Senda, T., and Ogasawara, M., (2000) J. Am. Chem. Soc., 122, 10716-10717;
28. Nishimura, K., Ono, M., Nagaoka, Y., and Tomioka, K. (2001) Angew. Chem. Int. Ed., 40, 440-442;
29. Sibi, M.P., Petrovic, G., and Zimmerman, J. (2005) J. Am. Chem. Soc., 127, 2390-2391;
30. Li, B.-J., Jiang, L., Liu, M., Chen, Y.-C., Ding, L.-S., and Wu, Y. (2005) Synlett, 603-606;
31. Leow, D., Lin, S., Chittimalla, S.K., Fu, X., and Tan, C.-H. (2008) Angew. Chem. Int. Ed., 47, 5641-5645.
32. Pracejus, H., Wilcke, F.-W., and Hanemann, K. (1977) J. Prakt. Chem., 319, 219-229.
33. Kumar, A., Salunkhe, R.V., Rane, R.A., and Dike, S.Y. (1991) J. Chem. Soc., Chem. Commun., 485-486.
34. Henze, R., Duhamel, L., and Lasne, M.-C. (1997) Tetrahedron: Asymmetry, 8, 3363-3365.
35. Perrard, T., Plaquevent, J.-C., Desmurs, J.-R., and Hebrault, D. (2000) Org. Lett., 2, 2959-2962.
36. Wang, Y., Liu, X., and Deng, L. (2006) J. Am. Chem. Soc., 128, 3928-3930.
37. Wang, B., Wu, F., Wang, Y., Liu, X., and Deng, L. (2007) J. Am. Chem. Soc., 129, 768-769.
38. Blanchet, J., Baudoux, J., Amere, M., Lasne, M.-C., and Rouden, J. (2008) Eur. J. Org. Chem., 5493-5506.
39. Marckwald, W. (1904) Ber. Dtsch. Chem. Ges., 37, 349-354;
40. Marckwald, W. (1904) Ber. Dtsch. Chem. Ges., 37, 1368-1370.
41. Toussaint, O., Capdevielle, P., and Maumy, M. (1987) Tetrahedron Lett., 28, 539-542.
42. Brunner, H. and Kurzwart, M. (1992) Monatsh. Chem., 123, 121-128.
43. Detalle, J.-F., Riahi, A., Steinmetz, V., Henin, F., and Muzart, J. (2004) J. Org. Chem., 69, 6528-6532.
44. Henin, F. and Muzart, J. (1992) Tetrahedron: Asymmetry, 3, 1161-1164;
45. Aboulhoda, S.J., Henin, F., Muzart, J., Thorey, C., Behnen, W., Martens, J., and Mehler, T. (1994) Tetrahedron: Asymmetry, 5, 1321-1326;
46. Aboulhoda, S.J., Letinois, S., Wilken, J., Reiners, I., Henin, F., Martens, J., and Muzart, J. (1995) Tetrahedron: Asymmetry, 6, 1865-1868;
47. Muzart, J., Henin, F., and Aboulhoda, S.J. (1997) Tetrahedron: Asymmetry, 8, 381-389;
48. Aboulhoda, S.J., Reiners, I., Wilken, J., Henin, F., Martens, J., and Muzart, J. (1998) Tetrahedron: Asymmetry, 9, 1847-1850.
49. Except in one particular example where 99% ee was obtained, see Muzart, J., Henin, F., and Aboulhoda, S.J. (1997) Tetrahedron: Asymmetry, 8, 381-389.
50. Roy, O., Diekmann, M., Riahi, A., Henin, F., and Muzart, J. (2001) Chem. Commun., 533-534;
51. Roy, O., Riahi, A., Henin, F., and Muzart, J. (2002) Eur. J. Org. Chem., 3986-3994.
52. Roy, O., Loiseau, F., Riahi, A., Henin, F., and Muzart, J. (2003) Tetrahedron, 59, 9641-9648.
53. Baur, M.A., Riahi, A., Henin, F., and Muzart, J. (2003) Tetrahedron: Asymmetry, 14, 2755-2761.
54. Kukula, P., Matousek, V., Mallat, T., and Baiker, A. (2007) Tetrahedron: Asymmetry, 18, 2859-2868.
55. Kukula, P., Matousek, V., Mallat, T., and Baiker, A. (2008) Chem. Eur. J., 14, 2699-2708.
56. Darensbourg, D.J., Holtcamp, M.W., Khandelwal, B., and Reibenspies, J.H. (1994) Inorg. Chem., 33, 531-537;
57. Darensbourg, D.J., Holtcamp, M.W., Khandelwal, B., Klausmeyer, K.K., and Reibenspies, J.H. (1995) Inorg. Chem., 34, 2389-2398.
58. Brunner, H., Müler, J., and Spitzer, J. (1996) Monatsh. Chem., 127, 845-858.
59. Henin, F., Muzart, J., Nedjima, M., and Rau, H. (1997) Monatsh. Chem., 128, 1181-1188.
60. Ryu, S.U. and Kim, S.Y.G. (1998) J. Ind. Eng. Chem., 4, 50-57.
61. Brunner, H. and Schmidt, P. (2000) Eur. J. Org. Chem., 2119-2133.
62. Brunner, H. and Baur, M.A. (2003) Eur. J. Org. Chem., 2854-2862.
63. Rogers, L.M.-A., Rouden, J., Lecomte, L., and Lasne, M.-C. (2003) Tetrahedron Lett., 44, 3047-3050;
64. Seitz, T., Baudoux, J., Bekolo, H., Cahard, D., Plaquevent, J.-C., Lasne, M.-C., and Rouden, J. (2006) Tetrahedron, 62, 6155-6165.
65. Martin, J., Lasne, M.-C., Plaquevent, J.-C., and Duhamel, L. (1997) Tetrahedron Lett., 38, 7181-7182.
66. Amere, M., Lasne, M.-C., and Rouden, J. (2007) Org. Lett., 9, 2621-2624.
67. McCooey, S.H. and Connon, S.J. (2005) Angew. Chem. Int. Ed., 44, 6367-6370.
68. Piva, O., Mortezaei, R., Henin, F., Muzart, J., and Pete, J.-P. (1990) J. Am. Chem. Soc., 112, 9263-9272;
69. Piva, O. and Pete, J.-P. (1990) Tetrahedron Lett., 31, 5157-5160.
70. Henin, F., M'Boungou-M'Passi, A., Muzart, J., and Pete, J.-P. (1994) Tetrahedron, 50, 2849-2864.
71. Ono, T., Kuhkar, V.P. and Soloshonok, V.A. (1996) J. Org. Chem., 61, 6563-6569;
72. Soloshonok, V.A. and Berbasov, D.O. (2004) J. Fluorine Chem., 125, 1757-1763.
73. Soloshonok, V.A. and Kuhkar, V.P. (1996) Tetrahedron, 52, 6953-6964;
74. Soloshonok, V.A., Kirilenko, A.G., Galushko, S.V., and Kuhkar, V.P. (1994) Tetrahedron Lett., 35, 5063-5064.
75. Michaut, V., Metz, F., Paris, J.-M., and Plaquevent, J.-C. (2007) J. Fluorine Chem., 128, 500-506.