Chiral bipyridine derivatives in asymmetric catalysis

Current Organic Chemistry

Volumn 7, Issue 17, 2003, Pages 1737-1757

  Malkov, A V ^a   Kocvsky P ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; SUBSTITUTION REACTIONS;

'CURRENT; ALLYLIC OXIDATION; ASYMMETRIC CATALYSIS; BIPYRIDINES; COPPER-CATALYZED CYCLOPROPANATION; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSIS; STERIC PROPERTIES; STRUCTURAL TYPE; SYNTHETIC APPROACH;

ALLYLATION;

ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; BIPYRIDINE DERIVATIVE; COPPER; KETONE DERIVATIVE; LIGAND; NITROGEN; OXIDE; PALLADIUM; SILANE DERIVATIVE;

ALKYLATION; ALLYLATION; ALLYLIC REARRANGEMENT; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; CYCLOPROPANATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; OXIDATION; PHYSICAL CHEMISTRY; REACTION ANALYSIS; REVIEW;

EID: 0141955242     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033486215     Document Type: Review

References (126)

1. (a) Togni, A.; Venanzi, L.M. Angew. Chem., Int. Ed. 1994 33, 497.
2. (b) Fache, F.; Schulz, E.; Tommasino, M.L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
3. For a review, see Pfaltz, A. Acta. Chem. Scand. 1994, 33, 497.
4. (a) McKenzie, P. Coord. Chem. Rev. 1971, 6, 187.
5. (b) Reedijk, J. In Comprehensive Coordination Chemistry (Wilkinson, G.; Gillard, R.D.; McClaverty, J.A., Eds.); Pergamon Oxford, 1987; Vol 2, p. 73.
6. (c) Bolm, C. In Organic Synthesis Via Organometallics (Hoffmann, R. W.; Dötz, K. H. Eds.), Vieweg: Braunschweig, 1990.
7. (a) Bottegi, C.; Caccia, G.; Chelucci, G.; Soccolini, F. J. Org. Chem. 1984, 49, 4290.
8. (b) Chelucci, G.; Cabras, M. A.; Bottegi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 855.
9. Bottegi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Organomet. Chem. 1986, 304, 217.
10. Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chessa, G. J. Organomet. Chem. 1989, 370, 285.
11. Lee, W.-S.; Kwong, H.-L.; Chang, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry, 2001, 12, 1007.
12. Kwong, H.-L.; Lee, W.-S. Tetrahedron: Asymmetry, 1999, 10, 3791.
13. Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber., 1992, 125, 1169.
14. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem. 1995, 60, 5386.
15. Uenishi, J.; Nishiwaki, K.; Hata, S. Tetrahedron Lett., 1994, 35, 7973.
16. Kandzia, C.; Steckhan, E.; Knoch, F. Tetrahedron: Asymmetry, 1993, 4, 39.
17. Peña-Cabrera, E.; Norrby, P.-O.; Sjörgen, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkemark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299.
18. Gladiali, S.; Chelucci, G.; Chessa, G.; Delogu, G.; Soccolini, F. J. Organomet. Chem. 1987, 327, C15.
19. Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry, 1990, 1, 635.
20. Chelucci, G. Synth. Commun. 1993, 23, 1897.
21. Weijenm, J. G. J.; Koudijs, A.; Endbersen, J. F.-J. J. Org. Chem. 1992, 57, 7258.
22. Gladiali, S.; Pinna, L.; Delogu, G.; Graf, E.; Brunner, H. Tetrahedron: Asymmetry, 1990, 1, 937.
23. Hayoz, P.; Von Zelewsky, A. Tetrahedron Lett., 1992, 33, 5165.
24. Chelucci, G.; Pinna, G.A.; Saba, A. Tetrahedron: Asymmetry, 1998, 9, 531.
25. Collomb, P.; Von Zelewsky, A. Tetrahedron: Asymmetry, 1998, 9, 3911.
26. Lotscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; Von Zelewsky, A. Tetrahedron: Asymmetry, 2000, 11, 4341.
27. Chelucci, G.; Saba, A.; Sanna, M. G.; Soccolini, F. Tetrahedron: Asymmetry, 2000, 11, 3427.
28. Malkov, A. V.; Baxendale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russel, D. R.; Mansfield, D. J.; Valko, M.; Kočvský, P. Organometallics 2001, 20, 673.
29. (a) Riesgo, E. C.; Credi, A.; De Cola, L.; Thummel, R. P. Inorg. Chem., 1998, 37, 2145.
30. (b) Gladiali, S.; Chelucci, G.; Madadu, M. T.; Gastaut, M. G.; Thummel, R. P. J. Org. Chem., 2001, 66, 400.
31. (c) Chelucci, G.; Pinna, G. A.; Saba, A.; Sanna, G. J. Mol. Catal. A, 2000, 159, 423.
32. (d) Chelucci, G.; Thummel, R. P. Synth. Commun., 1999, 29, 1665.
33. Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G. Applied Organomet. Chem. 1988, 2, 227.
34. Malkov, A. V.; Pernazza, D.; Bell, M.; Bella, M.; Massa, A.; Teplý, F.; Meghani, P.; Kočvský, P. J. Org. Chem., 2003, 68, 4727.
35. Knof, U.; Von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303.
36. Chelucci, G.; Saba, A. Tetrahedron: Asymmetry, 1998, 9, 2575.
37. For a review, see: Chelucci, G. Tetrahedron: Asymmetry, 1995, 6, 811.
38. Kröhnke, F. Synthesis, 1976, 1.
39. Gianini, M.; Von Zelewsky, A. Synthesis, 1996, 702.
40. Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett., 2001, 42, 3045.
41. Brown, H. C.; Weismann, S. A.; Perumal, P. T.; Dhokte, U. P. J. Org. Chem. 1990, 55, 1217.
42. (a) Mongin, F.; Trecout, F.; Mongin, O.; Queguiner, G. Tetrahedron, 2002, 58, 309.
43. (b) Schwab, P. F. H.; Fiescher, F.; Michl, J. J. Org. Chem. 2002, 67, 443.
44. Dietrich-Buchecker, C. O.; Marnot, P. A.; Sauvage, J. P. Tetrahedron Lett., 1982, 23, 5291.
45. Wörsdörfer, U.; Vöglte, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis, 1999, 597.
46. Wörsdörfer, U.; Vögtle, F.; Glorius, F.; Pflatz, A. J. Prakt. Chem. 1999, 341, 445.
47. Chelucci, G.; Falorini, M.; Giacomelli, G.; Tetrahedron, 1992, 48, 3653.
48. (a) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. Int. Ed. 1990, 29, 205.
49. (b) Rahm, F.; Stranne, R.; Bremberg, U.; Nordström, K.; Cernerud, M.; Macedo, E.; Moberg, C. J. Chem. Soc., Perkin Trans 1, 1, 2000, 1983.
50. Nishiyama, H.; Yamaguchi, S.; Park, S-B.; Itoh, K. Tetrahedron: Asymmetry, 1993, 4, 143.
51. Kwong, H.-L.; Cheng, L.-S.; Lee, W.-S.; Wong, W.-L.; Wong, W.-T. Eur. J. Inorg. Chem., 2000, 1997.
52. Bolm, C.; Ewald, M.; Zehnder, M.; Neuburger, M. A. Chem. Ber., 1992, 125, 453.
53. Ito, K.; Tabuchi, S.; Katsuki, T.; Synlett, 1992, 575.
54. Ito, K.; Katsuki, T. Tetrahedron Lett., 1993, 34, 2661.
55. Ito, K.; Katsuki, T. Chem. Lett., 1994, 1857.
56. Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron, 1996, 52, 3905.
57. Fletcher, N.C.; Keene, F.R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; Von Zelewsky, A. Helv. Chim. Acta, 1996, 79, 1192.
58. Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Org. Lett., 2000, 2, 3047.
59. Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; Von Zelewsky, A. Eur. J. Inorg. Chem., 2001, 1207.
60. Lotscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; Von Zelewsky, A.; Burger, P. Inorg. Chem., 2001, 40, 5675.
61. Ziegler, M.; Monney, H.; Stoeckli-Evans, H.; Von Zelewsky, A.; Sasaki, I.; Dupic, G.; Daran, J.-C.; Balavoine, G. G. A. J. Chem. Soc., Dalton Trans. 1999, 667.
62. Kwong, H.-L.; Lee, W.-S. Tetrahedron: Asymmetry, 2000, 11, 2299.
63. Chelucci, G.; Saba, A.; Vignola, D.; Solinas, C. Tetrahedron, 2001, 57, 1099.
64. Pezet, F.; Sasaki, I.; Daran, J.-C.; Hydro, J.; Aït-Haddou, H.; Balavoine, G. Eur. J. Inorg. Chem., 2001, 2669.
65. Kwong, H.-L.; Wong, W.-L.; Lee, W.-S.; Cheng, L.-S.; Wong, W.-T. Tetrahedron: Asymmetry, 2001, 12, 2683.
66. Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. A, 2002, 178, 27.
67. Alpha, B.; Anklam, E.; Deschenaux, R.; Lehn, J.-M.; Pietraskewicz, M. Helv. Chim. Acta, 1988, 71, 1042.
68. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis, 1984, 736.
69. Cassol, T.; Demnitz, F. W. J.; Navarro, M.; Neves, E. A. Tetrahedron Lett., 2000, 41, 8203.
70. Hassan, J.; Pennlva, V.; Lavenot, L.; Gozzi, C.; Lemaire, M. Tetrahedron, 1998, 54, 13793.
71. Mongin, F.; Trecourt, F.; Mongin, O.; Queguiner, G. Tetrahedron, 2002, 58, 309.
72. For the method, see Kozikowski, A. P.; Reddy, E. R.; Miller, C. P. J. Chem. Soc. Perkin Trans. 1, 1990; 195.
73. Ahmed, S.; Boruah, R. C. Tetrahedron Lett., 1996, 37, 8231.
74. Keuper, R.; Risch, N. Eur. J. Org. Chem. 1998, 2609.
75. Chelucci, G.; Saba, A. Synth. Commun. 2001, 31, 3161
76. Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett., 2002, 43, 3601.
77. Varela, J. A.; Castedo, L.; Saa, C. J. Am. Chem. Soc. 1998, 120, 12147.
78. For general methods, see Belser, P.; Bernhard, S.; Guerig, U. Tetrahedron, 1996, 52, 2937.
79. (a) Sasaki, H.; Irie, R.; Katsuki, T. Synlett, 1994, 356.
80. (b) Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron, 1994, 50, 11827.
81. Harmata, M.; Ghosh, S. K. Org. Lett., 2001, 3, 3321.
82. Kagan, H. B. In Comprehensive Asymmetric Catalysis (Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.); Springer-Verlag, 1999; Vol 1, p. 9.
83. Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun., 2000, 377.
84. Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 10270.
85. Wong, H. L.; Tian, Y.; Chan, K. C. Tetrahedron Lett., 2000, 41, 7723.
86. (a) Ford, A.; Sinn, E.; Woodward, S. J. Chem. Soc., Perkin Trans. 1, 1997; 927.
87. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis, 1999, 429.
88. (a) Bottegi, C.; Schionato, A.; De Lucci, O. Synth. Commun. 1991, 21, 1819. For a related example, see
89. (b) Wang, H. C.; Cui, Y. X.; Mak, T. C. W.; Wong, H. N. C. Chem. Commun., 1990, 167.
90. Dai, L.; Zhou, Z.; Zhang, Y.; Ni, C.; Zhang, Z.; Zhou, Y. Chem. Commun., 1987, 1760.
91. Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419.
92. Nakajima, M.; Sasaki, Y.; Shiro, M.; Hashimoto, S. Tetrahedron: Asymmetry, 1997, 8, 341.
93. Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett., 2002, 4, 1047.
94. Denmark, S. E,; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
95. (a) Zhang, H. C.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002.
96. (b) Zhang, H. C.; Kwong, F. Y.; Tian, Y.; Chan, K. S. J. Org. Chem. 1998, 63, 6886.
97. Rozen, S.; Dayan, S. Angew. Chem., Int. Ed. 1999, 38, 3872.
98. Yavari, I.; Maghsoodlou, M. T.; Pourmossavi, A. J. Chem. Research (S). 1997, 212.
99. Arai, S.; Ishikura, M.; Yamagishi, T. J. Chem. Soc., Perkin Trans. 1, 1998, 1561.
100. Dumitrascu, F.; Mitan, C. I.; Draghici, C.; Caproiu, M. T.; Raileanu, D. Tetrahedron Lett., 2001, 42, 8379.
101. Chelucci, G.; Gladiali, S.; Sanna, M.G.; Brunner, H. Tetrahedron: Asymmetry, 2000, 11, 3419.
102. Kwong, H.-L.; Lee, W.-S.; Ng, H.-F.; Chiu, W.-H.; Wong, W.-T. J. Chem. Soc., Dalton Trans., 1998, 1043.
103. Ito, K.; Katsuki, T.; Synlett, 1993, 638.
104. For overviews, see Andrus, M. B.; Lashley, J. Tetrahedron. 2002, 58, 845.
105. Eames, J.; Watkinson, M. Angew. Chem. Int. Ed. 2001, 40, 3567.
106. Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806.
107. For an overview, see Trost, B.M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
108. For representative papers, see (a) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
109. (b) Trost, B. M.; Dogra, K.; Hachiya, I.; Emura, T.; Hughes, D.L.; Krska, S.; Reamer, R.; Palucki, M.; Yasuda, N.; Reider, P. J. Angew. Chem. 2002, 41, 1929.
110. (c) Glorius, F.; Neuburger, M.; Pfaltz, A. Helv. Chim. Acta, 2001, 84, 3178.
111. (d) Malkov, A. V.; Spoor, P.; Vinader, V.; Kočovský, P. Tetrahedron Lett. 2001, 42, 509.
112. Malkov, A. V.; Baxendale I. R.; Mansfield D. J.; Kočovský, P. J. Chem. Soc., Perkin Trans 1, 2001, 1234.
113. Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry, 1999, 10, 2045.
114. Bottegi, C.; Schionato, A.; Chelucci, G.; Brunner, H.; Kürzinger, A.; Obermann, U. J. Organomet. Chem. 1989, 370, 17.
115. (a) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics, 1989, 8, 846.
116. (b) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics, 1991, 10, 500.
117. For an overview, see Dalko, P.I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726.
118. (a) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620;
119. (b) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161.
120. Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett., 2002, 4, 2799.
121. (a) Bolm, C.; Ewald, M. Tetrahedron Lett., 1990, 31, 5011;
122. (b) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber., 1992, 125, 1205.
123. (a) Saito, M.; Nakajima, M.; Hashimoto, S. Chem. Commun., 2000, 1851.
124. (b) Saito, M.; Nakajima, M.; Hashimoto, S. Tetrahedron, 2000, 56, 9589.
125. Nakajima, M.; Yamaguchi, Y.; Hashimoto, S. Chem. Commun., 2001, 1596.
126. Kwong, H-L.; Lau, K.-M.; Lee, W.-S.; Wong, W.-T. New J. Chem., 1999, 23, 629.