Ligands derived from carbohydrates for asymmetric catalysis

Chemical Reviews

Volumn 104, Issue 6, 2004, Pages 3189-3215

  Diëguez, Montserrat ^a   Pàmies, Oscar ^a   Claver, Carmen ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSIS; CYCLOPROPANATION; HECK REACTION; HETERODONOR; HYDROBORATION; HYDROFORMYLATION; HYDROSILYLATION; LIGANDS; PHOSPHINE LIGANDS;

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; DERIVATIVES; HYDROGENATION; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; OLEFINS; ORGANOMETALLICS; PHOSPHORUS COMPOUNDS; SUBSTITUTION REACTIONS;

CARBOHYDRATES;

CARBOHYDRATE; HYDROGEN; LIGAND;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; REVIEW; STEREOISOMERISM; SYNTHESIS;

CARBOHYDRATES; CATALYSIS; HYDROGEN; HYDROGENATION; LIGANDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 4344684124     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr0306889     Document Type: Article

References (212)

1. See, for example: Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. Ojima, I. Catalytic Asymmetric Synthesis; Wiley: New York, 2000.
3. Jaobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999.
4. Blaser, H.-U. Chem. Rev. 1992, 92, 935.
5. RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535.
6. Ayers, T. A.; RajanBabu, T. V. In Process Chemistry in the Pharmaceutical Industry; Gadamasetti, K. G., Ed.; Dekker: New York, 1999; pp 327-345.
7. Chen, M.; Lu, S. Fenzi Cuihua 2000, 14, 441.
8. Liu, X.; Wang, Y.; Miao, Q.; Jin, Z. Youji Huaxue 2001, 21, 191.
9. Ohe, K.; Yonehara, K.; Uemura, S. Yuki Gosei Kagaku Kyokaishi 2001, 59, 185.
10. RajanBabu, T. V. Chem. Rev. 2003, 103, 2645.
11. For recent reviews on carbohydrate complexes, see: Gyurcsik, B.; Nagy, L. Coord. Chem. Rev. 2000, 203, 81.
12. Steinborn, D.; Junicke, H. Chem. Rev. 2900, 100, 4283.
13. The use of carbohydrate-based ligands for metal-catalyzed asymmetric hydrocyanation and hydrovinylation has been recently reviewed by RajanBabu and co-workers, see, for example: refs 1c, 2b, 2c, 2g.
14. Kagan, H. N.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6430.
15. Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326.
16. Nagel, U.; Rieger, B. Organometallics 1989, 8, 1534.
17. Lafont, D.; Sinou, D.; Descotes, G. J. Organomet. Chem. 1979, 169, 87.
18. Bakos, J.; Heil, B.; Markó, L. J. Organomet. Chem. 1983, 253, 249.
19. Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62.
20. Habus, I.; Raza, Z.; Sunjić, V. Croat. Chim. Acta 1988, 61, 857.
21. Sunjić, V.; Habus, I.; Comisso, G.; Moimas, F. Gazz. Chim. Ital. 1989, 119, 229.
22. Li, C.; Bernet, B.; Vasella, A.; Broger, E. A.; Meili, A. Carbohydr. Res. 1991, 149.
23. Choudary, B. M.; Sarma, M. R.; Prasad, A. D.; Narender, N. Indian J. Chem. B 1994, 33, 152.
24. Gilbertson, S. R.; Chang, C. W. T. J. Org. Chem. 1995, 60, 6226.
25. Brunner, H.; Sievi R. J. Organomet. Chem. 1987, 328, 71.
26. Brunner, H.; Pieronczyk, W. J. Chem. Res. (S) 1980, 76.
27. Yamashita, M.; Hiramatsu, K.; Yamada, M.; Suzuki, N.; Inokawa, S. Bull. Chem. Soc. Jpn. 1982, 55, 2917.
28. Saito, S.; Nakamura, Y.; Morita, Y. Chem. Pharm. Bull. 1985, 33, 5284.
29. Iida, A.; Yamashita, M. Bull. Chem. Soc. Jpn. 1988, 61, 2365.
30. Lemaux, P.; Massonneau, V.; Simonneaux, G. J. Organomet. Chem. 1985, 284, 101.
31. Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
32. Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29.
33. Selke, R. React. Kinet. Catal. Lett. 1979, 10, 135.
34. Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213.
35. Selke, R. J. Prakt. Chem. 1987, 329, 717.
36. Selke, R. J. Organomet. Chem. 1989, 370, 249.
37. Selke, R.; Schwarze, M.; Baudisch, H.; Grassert, I.; Michalik, M.; Oehme, G.; Stoll, N.; Costisella, B. J. Mol. Catal. 1993, 84, 223.
38. Sinou, D.; Descotes, G. React. Kinet. Catal. Lett. 1980, 14, 463.
39. RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265.
40. Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
41. Habuš, I.; Raza, Z.; Šunjić, V. J. Mol. Catal. 1987, 42, 173.
42. Snatze, G.; Raza, Z.; Habuš, I.; Šunjić, V. Carbohydr. Res. 1988, 182, 179.
43. Yamashita, M.; Naoi, M.; Imoto, H.; Oshikawa, T. Bull. Chem. Soc. Jpn. 1989, 62, 942.
44. Yamashita, M.; Kobayashi, M.; Sigiura, M.; Tsunekawa, K.; Oshikawa, T.; Inokawa, S.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1986, 59, 175.
45. Bendayan, A.; Masotti, H.; Peiffer, G.; Siv, C.; Archavlis, A. J. Organomet. Chem. 1993, 444, 41.
46. Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kühnle. F. N. M.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta 1995, 78, 1636.
47. Wink, D. J.; Kwok, T. J.; Yee, A. Inorg. Chem. 1990, 29, 5006.
48. Sakaki, J.; Schweizer, W. B.; Seebach, D. Helv. Chim. Acta 1993, 76, 2654.
49. Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625.
50. Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijk, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 8, 719.
51. James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927.
52. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
53. See, for instance: Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99.
54. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363.
55. Masaki, Y.; Oda, H.; Kazuta, K.; Usui, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089.
56. Spescha, M. Helv. Chim. Acta 1993, 76, 1832.
57. Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692.
58. See, for instance: Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
59. Reetz, M. T.; Sell, T.; Meiswinkel, A.; Mehler, G. Angew Chem., Int. Ed. 2003, 42, 790.
60. Hu, W.; Chen, C. C.; Xue, G.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 4183.
61. Robert, F.; Oehme, G.; Sinou, D. J. Mol. Catal. A: Chem. 1999, 139, 105.
62. Guillaneux, D.; Martiny, L.; Kagan, H. B. Collect. Czech. Chem. Commun. 2000, 65, 717.
63. Yan, Y. Y.; RajanBabu, T. V. Org. Lett. 2000, 2, 4137.
64. Li, W.; Zhang, X. J. Org. Chem. 2000, 65, 5871.
65. Zhang, X. U.S. Patent WO 01/34612 A2, 2001.
66. Li, W.; Waldkirch, J. P.; Zhang, X. J. Org. Chem. 2002, 67, 7618.
67. Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
68. Holz, J.; Stürmer, R.; Schmidt, U.; Drexler, H. J.; Heller, D.; Krimmer, H. P.; Börner, A. Eur. J. Org. Chem. 2001, 4615.
69. Stürner, R.; Klatt, M. J.; Börner, A.; Holz, J.; Voss, G. U.S. Patent 6359165 B1, 2002.
70. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
71. Liu, D.; Li, W.; Zhang, X. Org. Lett. 2002, 4, 4471.
72. Zhang, X. Patent WO 03/040149 A2, 2003.
73. Bayer, A.; Murszat, P.; Thewalt, U. Rieger, B. Eur. J. Inorg. Chem. 2002, 2614.
74. Carmichael, D.; Doucet, H.; Brown, J. M. Chem. Commun. 1999, 261.
75. Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059.
76. RajanBabu, T. V.; Yan, Y. Y.; Shin, S. J. Am. Chem. Soc. 2001, 123, 10207.
77. Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Eur. J. Inorg. Chem. 2000, 2011.
78. Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillón, S.; Claver, C. Tetrahedron: Asymmetry 2000, 11, 4701.
79. RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
80. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
81. Ayers, T. A.; RajanBabu, T. V. U.S. Patent 5510507, 1996.
82. Yan, Y. Y.; RajanBabu, T. V. J. Org. Chem. 2001, 66, 3277.
83. Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967.
84. Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381.
85. Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593.
86. Shin, S.; Rajan-Babu, T. V. Org. Lett. 1999, 1, 1229.
87. Chen, Y.; Li, X.; Tong, S.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957.
88. Faltin, F.; Fehring, V.; Kadyrov, R.; Arrieta, A.; Schareina, T.; Selke, R.; Miethchen, R. Synthesis 2001, 638.
89. Guimet, E. Masters Thesis, Universitat Rovira i Virgili, 2001.
90. Kadyrov, R.; Heller, D.; Selke, R. Tetrahedron: Asymmetry 1999, 9, 329.
91. Reetz, M. T.; Neugebauer, T. Angew. Chem., Int. Ed. 1999, 38, 179.
92. Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Eur. J. Inorg. Chem. 2000, 1287.
93. Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2000, 11, 1097.
94. Diéguez, M.; Ruiz, A.; Claver, C. J. Org. Chem. 2002, 67, 3796.
95. Diéguez, M.; Ruiz, A.; Claver, C. Dalton Trans. 2003, 2957.
96. Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 961.
97. Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941.
98. Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889.
99. Reetz, M. T.; Goosen, L. J.; Meiswinkel, A.; Paetzol, J.; Jensen, J. F. Org. Lett. 2003, 5, 3099.
100. Huang, H.; Zheng, Z.; Luo, H.; Bai, C.; Hu, X.; Chen, H. Org. Lett. 2003, 5, 4137.
101. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Maljaars, C. E. P.; Willans, C. E.; Hyett, D.; Boogers, J. A. F.; Henderick, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 308.
102. Diéguez, M.; Orejón, A.; Masdeu-Bultó, A. M.; Echarri, R.; Castillón, S.; Claver, C.; Ruiz, A. J. Chem. Soc., Dalton Trans. 1997, 4611.
103. Diéguez, M.; Ruiz, A.; Claver, C.; Pereira, M. M.; Rocha Gonsalves, M. d'A. J. Chem. Soc., Dalton Trans. 1998, 3517.
104. Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Chem. Soc., Dalton Trans. 1999, 3439.
105. Flores-Santos, L.; Martin, E.; Aghmiz, A.; Diéguez, M.; Claver, C.; Masdeu-Bultó, A. M.; Munoz-Hernández, M. A. Manuscript in preparation.
106. Reetz, M. T.; Gosberg, A. Tetrahedron: Asymmetry 1999, 10, 2129.
107. Ohe, K.; Morioka, K.; Yonehara, K.; Uemura, S. Tetrahedron: Asymmetry 2002, 13, 2155.
108. Robert, F.; Sinou, D. J. Organomet. Chem. 2000, 604, 99.
109. Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. Organometallics 2000, 19, 1488.
110. Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. Chem. Commun. 2000, 2383.
111. Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364.
112. Diéguez, M.; Ruiz, A.; Claver, C. Chem. Commun. 2001, 2702.
113. Hildraf, R.; Pfaltz, A. Synlett 1999, 1814.
114. Tatarov, V. I.; Kadirov, R.; Riermeier, T. H.; Holz, J.; Börner, A. Tetrahedron: Asymmetry 1999, 10, 4009.
115. Guiu, E.; Munoz, B.; Castellón, S.; Claver, C. Adv. Synth. Catal. 2003, 345, 169.
116. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpainter, C. W. J. Mol. Catal. 1995, 104, 17.
117. Agboussou, F.; Carpentier, J. F.; Mortreux, A. Chem. Rev. 1995, 95, 2485;
118. Gladiali, S.; Bayón, J.; Claver, C. Tetrahedron: Asymmetry 1995, 7, 1453.
119. van Leeuwen, P. W. N. M.; Claver, C. Rhodium Catalyzed Hydroformylation; Kluwer Academic Press: Dordrecht, 2000.
120. Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183.
121. Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046.
122. Diéguez, M.; Pereira, M. M.; Masdeu Bultó, A. M.; Claver, C.; Bayón, J. C. J Mol. Catal. A: Chem. 1999, 143, 111 and references therein.
123. Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413.
124. Franció, G.; Leitner, W. Chem. Commun. 1999, 1663.
125. Babin, J. E.; Whiteker, G. T. WO 93/03839, 1993.
126. Buisman, G. J. H.; van der Veen, L. A.; Klootwijk, A.; der Lange, W. G. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Organometallics 1997, 16, 2929.
127. Liu, S.; Li, X.; Wang, A. Catal. Today 2000, 63, 531.
128. Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 651.
129. RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295.
130. Ayers, T. A.; RajanBabu, T. V. U.S. Patent 5475146, 1995.
131. Ayers, T. A.; RajanBabu, T. V. U.S. Patent 5574171, 1996.
132. Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillón, S.; Claver, C. Chem. Commun. 2000, 1607.
133. Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillón, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086.
134. Diéguez, M.; Pàmies, O.; Ruiz, A.; Claver, C. New. J. Chem. 2002, 26, 827.
135. Kless, A.; Holz, J.; Heller, D.; Kadirov, R.; Selke, R.; Fischer, C.; Börner, A. Tetrahedron: Asymmetry 1996, 7, 33.
136. Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885.
137. Aghmiz, A.; Masdeu-Bultó, A. M.; Claver, C.; Sinou, D. J. Mol. Catal. A: Chem. 2002, 184, 111.
138. Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441.
139. Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2827.
140. Orejón, A.; Masdeu-Bultó, A. M.; Diéguez, M.; Forniés-Cámer, J.; Claver, C.; Cardin, C. J. J. Organomet. Chem. 1998, 559, 23.
141. Diéguez, M.; Ruiz, A.; Claver, C.; Pereira, M. M.; Flor, M. T.; Bayón, J. C.; Serra, M. E. S.; Rocha Gonsalves, A. M. d'A. Inorg. Chim. Acta 1999, 295, 64.
142. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
143. Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1869.
144. For recent examples, see: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
145. Braunstein, P.; Naud, F. Angew. Chem., Int. Ed. 2001, 40, 680.
146. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
147. Masdeu-Bultó, A. M.; Diéguez, M.; Martin, E.; Gómez, M. Coord. Chem. Rev. 2003, 242, 159 and references therein.
148. Pàmies, O.; Ruiz, A.; Net, G.; Claver, C.; Kalchhauser, H.; Widhalm, M. Monatsch. Chem. 2000, 131, 1173.
149. Diéguez, M.; Jansat, S.; Gómez, M.; Ruiz, A.; Muller, G.; Claver, C. Chem. Commun. 2001, 1132.
150. Yan, Y. Y.; RajanBabu, T. V. Org. Lett. 2000, 2, 199.
151. Zhang, X. WO Patent 03/040149 A2, 2003.
152. Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745.
153. Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601.
154. Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867.
155. Jansat, S.; Gómez, M.; Muller, G.; Diéguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bultó, A. M.; Flores-Santos, L.; Martín, E.; Maestro, M. A.; Mahía, J. Tetrahedron: Asymmetry 2001, 12, 1469.
156. Khiar, N.; Araújo, C. S.; Alvarez, E.; Fernández, I. Tetrahedron Lett. 2003, 44, 3401.
157. Albinati, A.; Pregosin, P. S.; Wick, K. Organometallics 1996, 15, 2419.
158. Barbaro, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics 1996, 15, 1879.
159. Nakano, H.; Yokoyama, J.; Okuyama, Y.; Fujita, R.; Hongo, H. Tetrahedron: Asymmetry 2003, 14, 2361.
160. Robert, F.; Gaillard, N.; Sinou, D. J. Mol. Catal. A: Chem. 1999, 144, 473.
161. Borriello, C.; Cucciolito, M. E.; Panunzi, A.; Ruffo, F. Inorg. Chim. Acta 2003, 353, 238.
162. Brunner, H.; Schönherr, M.; Zabel, M. Tetrahedron: Asymmetry 2003, 14, 1115.
163. Gläser, B.; Kunz, H. Synlett 1998, 53.
164. Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. Chem. Commun. 1999, 415.
165. Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9374.
166. Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197.
167. Boog-Wick, K.; Pregosin, P. S.; Trabesinger, G. Organometallics 1998, 17, 3254.
168. For reviews, see: Alexakis, A. In Organocopper Reagents, A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; Chapter 8.
169. Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283.
170. Woodward, S. Chem. Soc. Rev. 2000, 29, 393.
171. Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
172. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
173. Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518.
174. Knöbel, A. K. H.; Escher, I. J.; Pfaltz, A. Synlett 1997, 1429.
175. Yan, M.; Yang, L. W.; Wong, K. Y.; Chan, A. S. C. Chem. Commun. 1999, 11.
176. Yan, M.; Zhou, Z. Y.; Chan, A. S. C. Chem. Commun. 2000, 115.
177. Chataigner, I.; Gennari, C.; Piarulli, U.; Ceccarelli, S. Angew. Chem., Int. Ed. 2000, 39, 916.
178. Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628.
179. Alexakis, A.; Burton, J.; Vastra, J.; Benhaim, C.; Fournioux, X.; van den Heuvel, A.; Levêque, J. M.; Mazé, F.; Rosset, S. Eur. J. Org. Chem. 2000, 4011.
180. Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579.
181. Alexakis, A.; Benhaim, C. Tetrahedron: Asymmetry 2001, 12, 1151.
182. Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 1999, 10, 2007.
183. Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2000, 11, 4377.
184. Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron:Asymmetry 2001, 12, 2895.
185. Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869.
186. Mandoli, A.; Arnold, L. A.; de Vries, A. H. M.; Salvadori, P.; Feringa, B. L Tetrahedron: Asymmetry 2001, 12, 1929.
187. Kelle, E.; Maurer, J.; Naasz, R.; Schader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron Asymmetry 1998, 9, 2409.
188. Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773.
189. Pigro, M. C.; Angiuoni, G.; Piancatelli, G. Tetrahedron 2002, 58, 5459.
190. Seebach, D.; Jaesche, G.; Pichota, A.; Audergon, L. Helv. Chim. Acta 1997, 80, 2515.
191. Pichota, A.; Pregosin, P. S.; Valentín, M.; Wörle, M.; Seebach, D. Angew. Chem., Int. Ed. 2000, 39, 153.
192. Pàmies, O.; Net, G.; Ruiz, A.; Claver, C.; Woodward, S. Tetrahedron: Asymmetry 2000, 11, 871.
193. Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861.
194. Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Catal. A: Chem. 2002, 185, 11.
195. Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. 2001, 40, 92.
196. Cho, B. T.; Kim, N. J. J. Chem. Soc., Perkin Trans. 1 1996, 2901.
197. Bauer, T.; Tarasiuk, J.; Pasniczek, K. Tetrahedron: Asymmetry 2002, 13, 77.
198. Huang, H.; Chen, H.; Hu, X.; Bai, C.; Zheng, Z. Tetrahedron: Asymmetry 2003, 14, 297.
199. Huang, H.; Zheng, Z.; Chen, H.; Bai, C.; Wang, J. Tetrahedron: Asymmetry 2003, 14, 1285.
200. Yonehara, K.; Mori, K.; Hashizume, T.; Chung, K. G.; Ohe, K.; Uemura, S. J. Organomet. Chem. 2000, 603, 40.
201. Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184.
202. Imbos, R.; Minnaard, A. J.; Feringa, B. L. Dalton Trans. 2003, 2017.
203. Blume, F.; Zemolka, S.; Fey, T.; Kranich, R.; Schmalz, H. G. Adv. Synth. Catal. 2002, 344, 868.
204. Recently other type of carbohydrate ligands have been applied with moderate success, see, for instance: Suárez, A.; Pizzanp, A.; Fernández, I.; Khiar, N. Tetrahedron: Asymmetry 2001, 12, 633.
205. Diéguez, M.; Pàmies, O.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2002, 13, 83.
206. Haag, D.; Runsink, J.; Schaf, H. D. Organometallics 1998, 17, 398.
207. Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096.
208. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
209. Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1996, 37, 4073.
210. Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518.
211. Harm, A. M.; Knight, J. G.; Stemp, G. Tetrahedron Lett. 1996, 37, 6189.
212. Borriello, C.; Cucciolito, M. E.; Panunzi, A.; Ruffo, F. Tetrahedron: Asymmetry 2001, 12, 2467.