Chiral 2,2′-bipyridines: Ligands for asymmetric induction

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 16, 2002, Pages 1831-1842

  Fletcher, Nicholas C ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035982148     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b204272j     Document Type: Review

References (116)

1. J. Reedijk, in Comprehensive Coordination Chemistry, ed. S. G. W. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon Press, Oxford, 1987.
2. E.C. Constable, P.J. Steel Coord. Chem. Rev. 1989, 93, 205.
3. A. Juris, S. Barigelletti, S. Campagna, V. Balzani, P. Belser, A. von Zelewsky Coord. Chem. Rev. 1988, 84, 85.
4. C. Kaes, A. Katz, M.W. Hosseini Chem. Rev. 2000, 100, 3553.
5. L.A. Summers, The Bipyridinium Herbicides, Academic Press, New York, 1980.
6. V. Balzani, A. Juris, M. Venturi, S. Campagna, S. Serroni Chem. Rev. 1996, 96, 759.
7. V. Balzani, P. Ceroni, A. Juris, M. Venturi, S. Campagna, F. Puntoriero, S. Serroni Coord. Chem. Rev. 2001, 219, 545.
8. V. Balzani and F. Scandola, Supramolecular Photochemistry, Ellis Horwood, Chichester, 1991.
9. M.H. Keefe, K.D. Benkstein, J.T. Hupp Coord. Chem. Rev. 2000, 205, 201.
10. P.D. Beer, J. Cadman Coord. Chem. Rev. 2000, 205, 131.
11. A. von Zelewsky, Stereochemistry of Coordination Compounds, Wiley, Chichester, 1996.
12. U. Knof, A. von Zelewsky Angew. Chem., Int. Ed. 1999, 38, 302.
13. M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli, M. Montanucci Synthesis 1984, 736.
14. M. Iyoda, H. Otsuka, K. Sato, N. Nisato, M. Oda Bull. Chem. Soc. Jpn. 1990, 63, 80.
15. T.M. Cassol, F.W.J. Demnitz, M. Navarro, E.A.D. Neves Tetrahedron Lett. 2000, 41, 8203.
16. C. Bolm, M. Zehnder, D. Bur Angew. Chem., Int. Ed. Engl. 1990, 29, 205.
17. C. Bolm, M. Ewald, M. Felder, G. Schlingloff Chem. Ber. 1992, 125, 1169.
18. C. Bolm, G. Schlingloff, K. Harms Chem. Ber. 1992, 125, 1191.
19. H.L. Kwong, W.S. Lee, H.F. Ng, W.H. Chiu, W.T. Wong J. Chem. Soc., Dalton Trans. 1998, 1043.
20. H.L. Kwong, K.M. Lau, W.S. Lee, W.T. Wong New J. Chem. 1999, 23, 629.
21. H.L. Kwong, W.S. Lee Tetrahedron: Asymmetry 1999, 10, 3791.
22. W.S. Lee, H.L. Kwong, H.L. Chan, W.W. Choi, L.Y. Ng Tetrahedron: Asymmetry 2001, 12, 1007.
23. G. Chelucci, V. Caria, A. Saba J. Mol. Catal. A, Chem. 1998, 130, 51.
24. G. Chelucci, N. Culeddu, A. Saba, R. Valenti Tetrahedron: Asymmetry 1999, 10, 3537.
25. F. Rahm, R. Stranne, U. Bremberg, K. Nordstrom, M. Cernerud, E. Macedo, C. Moberg J. Chem. Soc., Perkin Trans. 1 2000, 1983.
26. H.L. Wong, Y. Tian, K.S. Chan Tetrahedron Lett. 2000, 41, 7723.
27. R. Rios, J. Liang, M.M.C. Lo, G.C. Fu Chem. Commun. 2000, 377.
28. K. Ito, S. Tabuchi, T. Katsuki Synlett 1992, 575.
29. K. Ito, T. Katsuki Tetrahedron Lett. 1993, 34, 2661.
30. K. Ito, M. Yoshitake, T. Katsuki Tetrahedron 1996, 52, 3905.
31. A. von Zelewsky, P. Lainé Private communication.
32. B. Kolp, D. Abeln, H. Stoeckli-Evans, A. von Zelewsky Eur. J. Inorg. Chem. 2001, 1207.
33. N.C. Fletcher, F.R. Keene, M. Ziegler, H. Stoecklievans, H. Viebrock, A. von Zelewsky Helv. Chim. Acta 1996, 79, 1192.
34. A.V. Malkov, I.R. Baxendale, M. Bella, V. Langer, J. Fawcett, D.R. Russell, D.J. Mansfield, M. Valko, P. Kocovsky Organometallics 2001, 20, 673.
35. A.V. Malkov, M. Bella, V. Langer, P. Kocovsky Org. Lett. 2000, 2, 3047.
36. D. Lötscher, S. Rupprecht, P. Collomb, P. Belser, H. Viebrock, A. von Zelewsky, P. Burger Inorg. Chem. 2001, 40, 5675.
37. D. Lötscher, S. Rupprecht, H. Stoeckli-Evans, A. von Zelewsky Tetrahedron: Asymmetry 2000, 11, 4341.
38. S. Fraysse, A. von Zelewsky, H. Stoeckli-Evans New J. Chem. 2001, 25, 1374.
39. J.C.G. Bunzli, L.J. Charbonniere, R.F. Ziessel J. Chem. Soc., Dalton Trans. 2000, 1917.
40. N. Fletcher, M. Nieuwenhuyzen, S. Rainey J. Chem. Soc., Dalton Trans. 2001, 2641.
41. N. Garelli, P. Vierling J. Org. Chem. 1992, 57, 3046.
42. P.N.W. Baxter, J.A. Connor, J.D. Wallis, D.C. Povey, K. Powell J. Chem. Soc., Perkin Trans. 1 1992, 1601.
43. H. Nishiyama, S. Yamaguchi, S.B. Park, K. Itoh Tetrahedron: Asymmetry 1993, 4, 143.
44. R.B. Hopkins, A.D. Hamilton J. Chem. Soc., Chem. Commun. 1987, 171.
45. R.B. Hopkins, J.S. Albert, D. van Engen, A.D. Hamilton Bioorg. Med. Chem. 1996, 4, 1121.
46. D.R. Ahn, T.W. Kim, J.I. Hong J. Org. Chem. 2001, 66, 5008.
47. K. Ohkubo, T. Hamada, H. Ishida J. Chem. Soc., Chem. Commun. 1993, 1423.
48. K. Ohkubo, T. Hamada, H. Ishida, M. Fukushima, M. Watanabe, H. Kobayashi J. Chem. Soc., Dalton Trans. 1994, 239.
49. L.H. Uppadine, F.R. Keene, P.D. Beer J. Chem. Soc., Dalton Trans. 2001, 2188.
50. K. Ohkubo, T. Hamada, T. Inaoka, H. Ishida Inorg. Chem. 1989, 28, 2021.
51. S.G. Telfer, G. Bernardinelli, A.F. Williams Chem. Commun. 2001, 1498.
52. C. Kandzia, E. Steckhan, F. Knoch Tetrahedron: Asymmetry 1993, 4, 39.
53. C. Bolm, M. Ewald Tetrahedron Lett. 1990, 31, 5011.
54. C. Botteghi, G. Caccia, G. Chelucci, F. Soccolini J. Org. Chem. 1984, 49, 4290.
55. C. Botteghi, G. Chelucci, G. Chessa, G. Delogu, S. Gladiali, F. Soccolini J. Organomet. Chem. 1986, 304, 217.
56. C. Botteghi, A. Schionato, G. Chelucci, H. Brunner, A. Kurzinger, U. Obermann J. Organomet. Chem. 1989, 370, 17.
57. G. Chelucci, F. Soccolini, C. Botteghi Synth. Commun. 1985, 15, 807.
58. G. Minghetti, M.A. Cinellu, G. Chelucci, S. Gladiali, F. Demartin, M. Manassero J. Organomet. Chem. 1986, 307, 107.
59. F. Kröhnke Synthesis 1976, 1.
60. P. Hayoz, A. von Zelewsky Tetrahedron Lett. 1992, 33, 5165.
61. J. Moutet, C. Duboc-Toia, S. Menage, S. Tingry Adv. Mater. 1998, 10, 665.
62. A. von Zelewsky, O. Mamula J. Chem. Soc., Dalton Trans. 2000, 219.
63. P. Collomb, A. von Zelewsky Tetrahedron: Asymmetry 1998, 9, 3911.
64. G. Chelucci, G.A. Pinna, A. Saba Tetrahedron: Asymmetry 1998, 9, 531.
65. G. Chelucci, A. Saba, G. Sanna, F. Soccolini Tetrahedron: Asymmetry 2000, 11, 3427.
66. B. Imperiali, S.L. Fisher J. Am. Chem. Soc. 1991, 113, 8527.
67. B. Imperiali, S.L. Fisher J. Org. Chem. 1992, 39, 757.
68. B. Imperiali, T.J. Prins, S.L. Fisher J. Org. Chem. 1993, 58, 1613.
69. K.J. Kise, B.E. Bowler Tetrahedron: Asymmetry 1998, 9, 3319.
70. N. Nishino, T. Arai, J. Hayashida, H.I. Ogawa, H. Yamamoto, S. Yoshikawa Chem. Lett. 1994, 2435.
71. J. Uenishi, T. Hiraoka, S. Hata, K. Nishiwaki, O. Yonemitsu, K. Nakamura, H. Tsukube J. Org. Chem. 1998, 63, 2481.
72. H. Mürner, A. von Zelewsky, H. Stoeckli-Evans Inorg. Chem. 1996, 35, 3931.
73. O. Mamula, F.J. Monlien, A. Porquet, G. Hopfgartner, A.E. Merbach, A. von Zelewsky Chem. Eur. J. 2001, 7, 533.
74. O. Mamula, A. von Zelewsky, T. Bark, H. Stoeckli-Evans, A. Neels, G. Bernardinelli Chem. Eur. J. 2000, 6, 3575.
75. O. Mamula, A. von Zelewsky, T. Bark, G. Bernardinelli Angew. Chem., Int. Ed. Engl. 1999, 38, 2945.
76. G. Baum, E.C. Constable, D. Fenske, C.E. Housecroft, T. Kulke Chem. Eur. J. 1999, 5, 1862.
77. P. Baret, J. Einhorn, G. Gellon, J.L. Pierre Synthesis 1998, 431.
78. P. Baret, D. Gaude, G. Gellon, J.L. Pierre New J. Chem. 1997, 21, 1255.
79. G. Baum, E.C. Constable, D. Fenske, C.E. Housecroft, T. Kulke Chem. Commun. 1999, 195.
80. W. Zarges, J. Hall, J.-M. Lehn, C. Bolm Helv. Chim. Acta 1991, 74, 1843.
81. Y. Habata, J.S. Bradshaw, X.X. Zhang, R.M. Izatt J. Am. Chem. Soc. 1997, 119, 7145.
82. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, C.R. Woods, J.S. Siegel Eur. J. Org. Chem. 2001, 173.
83. C.R. Woods, M. Benaglia, F. Cozzi, J.S. Siegel Angew. Chem., Int. Ed. Engl. 1996, 35, 1830.
84. J. Hodacova, I. Stibor Collect. Czech. Chem. Commun. 2000, 65, 83.
85. R. Prabaharan, N.C. Fletcher, M. Nieuwenhuyzen J. Chem. Soc., Dalton Trans. 2001, 602.
86. M. Albrecht Chem. Rev. 2001, 101, 3457.
87. C. Piguet, G. Bernardinelli, G. Hopfgartner Chem. Rev. 1997, 97, 2005.
88. A. Werner, A. Vilmos Z. Anorg. Allg. Chem. 1899, 21, 145.
89. H. Mürner, A. von Zelewsky, G. Hopfgartner Inorg. Chim. Acta 1998, 271, 36.
90. E.Z. Jandrasics, F.R. Keene J. Chem. Soc., Dalton Trans. 1997, 153.
91. H.-R. Mürner, P. Belser, A. von Zelewsky J. Am. Chem. Soc. 1996, 118, 7989.
92. K. Ohkubo, T. Hamada, M. Watanabe J. Chem. Soc., Chem. Commun. 1993, 1070.
93. K. Ohkubo, T. Hamada, M. Watanabe, M. Fukushima Chem. Lett. 1993, 1651.
94. K. Ohkubo, M. Watanabe, H. Ohta, S. Usui J. Photochem. Photobiol., A 1996, 95, 231.
95. K. Ohkubo, M. Fukushima, H. Ohta, S. Usui J. Photochem. Photobiol., A 1996, 98, 137.
96. T. Hamada, H. Ohtsuka, S. Sakaki Chem. Lett. 2000, 364.
97. T. Hamada, H. Ohtsuka, S. Sakaki J. Chem. Soc., Dalton Trans. 2001, 928.
98. T. Hamada, B.S. Brunschwig, K. Eifuku, E. Fujita, M. Korner, S. Sakaki, R. van Eldik, J.F. Wishart J. Phys. Chem. A 1999, 103, 5645.
99. T. Hamada, S. Sakaki, B.S. Brunschwig, E. Fujita, J.F. Wishart Chem. Lett. 1998, 1259.
100. T. Hamada, H. Ishida, S. Usui, K. Tsumura, K. Ohkubo J. Mol. Catal. 1994, 88, L1.
101. T. Hamada, H. Ishida, S. Usui, Y. Watanabe, K. Tsumura, K. Ohkubo J. Chem. Soc., Chem. Commun. 1993, 909.
102. A. Togni, L.M. Venanzi Angew. Chem., Int. Ed. Engl. 1994, 33, 497.
103. C. Bolm, in Advances in Organic Synthesis via Organometallics, ed. R. W. Hoffmann and K. K. Dötz, Vieweg Verlag, Braunschweig, 1991.
104. H. Nozaki, H. Takaya, S. Moriuti, R. Noyori Tetrahedron Lett. 1966, 7, 5239.
105. A. Pfaltz, in Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999.
106. A. Pfaltz, in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 1998.
107. G. Chelucci, S. Gladiali, M.G. Sanna, H. Brunner Tetrahedron: Asymmetry 2000, 11, 3419.
108. N. Oguni, T. Omi Tetrahedron Lett. 1984, 25, 2823.
109. L. Pu, H.B. Yu Chem. Rev. 2001, 101, 757.
110. G. Zassinovich, G. Mestroni, S. Gladiali Chem. Rev. 1992, 92, 1051.
111. S. Gladiali, L. Pinna, G. Delogu, E. Graf, H. Brunner Tetrahedron: Asymmetry 1990, 1, 937.
112. J.C. Moutet, L.Y. Cho, C. Duboc-Toia, S. Menage, E.C. Riesgo, R.P. Thummel New J. Chem. 1999, 23, 939.
113. B.M. Trost, D.L. Van Vranken Chem. Rev. 1996, 96, 395.
114. M.S. Kharasch, G. Sosnovsky, N.C. Yang J. Am. Chem. Soc. 1959, 81, 5819.
115. M.D. Ward, J.A. McCleverty Dalton Trans. 2002, 275.
116. H. Weizman, J. Libman, A. Shanzer J. Am. Chem. Soc. 1998, 120, 2188.