Modified BINAP: The how and the why

Chemical Reviews

Volumn 105, Issue 5, 2005, Pages 1801-1836

  Berthod, Mikaël ^a   Mignani, Gérard ^b   Woodward, Gary ^c   Lemaire, Marc ^a  

^a UNIVERSITÉ LYON 1   (France)

^b Rhodia Europe   (France)

^c Rhodia PPD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CATALYST SELECTIVITY; CATALYSTS; CHEMICAL MODIFICATION; COMPOSITION EFFECTS; DERIVATIVES; GRAFTING (CHEMICAL); SILICA; SOLUBILITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; BINAPHTHYL MOIETY; FUNCTIONALIZATION; NOYORI/TAKASAGO METHOD; PHENYL MOIETY;

AROMATIC COMPOUNDS;

EID: 20044397048     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr040652w     Document Type: Review

References (195)

1. Knowles, W. S.; Sabacky, M. J. Chem. Commun. 1968, 1445.
2. Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
3. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
4. Research by topic on SciFinder Scholar, 24-8-27. Keyword BINAP and then refine by document type.
5. http://www.rhodia-ppd.com.
6. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
7. Takasago Perfumery Co., Ltd. Japanese Patent JP 59020294, 1984.
8. Takasago Perfumery Co., Ltd. European Patent EP 135392, 1984.
9. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
10. Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
11. Cai, D. (Merck). U.S. Patent US 252,306, 1994;
12. U.S. Patent US 5,399,771, 1995.
13. Tanaka, K.; Okada, T.; Toda, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1147.
14. Laneman, S. A. Chem. Commun. 1997, 2359.
15. Laneman, S. A. (Monsanto). U.S. Patent US 5,902,904, 1997.
16. Merck Darmstadt. PCT Int. Appl. WO 99/36397, 1999.
17. For a review see: Akutagawa, S. Appl. Catal., A 1995, 128, 171.
18. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994; Chapter 1.
19. (b) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993; Chapter 1.
20. (c) Takaya, H.; Ohta, T.; Mashima, K. Homogeneous Transition Metal Catalyzed Reactions.
21. (d) Moser, W. R., Slocum, D., Eds. Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; p 124.
22. (e) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
23. (f) Noyori, R.; Takaya, H. Chem. Soc.. 1985, 25, 83.
24. Bergens, S. H.; Nohada, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2121.
25. (a) Tani, K.; Yamagata, T.; Akutagawa, S.; Kumobayashi, H.; Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R.; Otsuka, S. J. Am. Chem. Soc. 1984, 16, 5208.
26. (b) Inoue, S.; Takaya, H.; Tani, K.; Otsuka, S.; Sato, T.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 4897.
27. Lubel, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543.
28. (a) Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174.
29. (b) Ohta, T.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1990, 31, 7189.
30. (a) Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117.
31. (b) Kitamura, M.; Hsiao, Y.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4829.
32. (c) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.
33. Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.-I.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596, 4129.
34. Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995,6, 357.
35. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
36. Kitamura, M.; Ohkuma, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
37. For a review see: Blaser, H. U.; Spindler, F.; Studer, M. Appl. Catal., A 2001, 221,119.
38. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Champion, N.; Deschaux, G.; Dellis, P. Org. Process Res. Dev. 2003, 7, 399.
39. Vallarino, L. J. Chem. Soc. 1957, 2287.
40. Sanger, A. J. Chem. Soc., Dalton Trans. 1977, 120.
41. Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
42. Allen, D. W.; Taylor, B. F. J. Chem. Soc., Dalton Trans. 1982, 51.
43. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Champion, N.; Deschaux, G.; Dellis, P. Tetrahedron Lett. 2003, 44, 823.
44. Takaya, H.; Ohta, T.; Noyori, R.; Yamada, N.; Akutagawa, S.; Takazawa, T.; Sayo, N.; Taketomi, T.; Kumobayashi, H. (Takasago Perfumery Co., Ltd.). European Patent Appl. EP 0245959, 1987.
45. Ohta, T.; Noyori, R.; Takatani, H.; Akutagawa, S.; Kitamura, M.; Nagai, K.; T.; Sayo, N.; Taketomi, T.; Kumobayashi, H. (Takasago International Corp.). Japanese Patent JP 64068386, 1989.
46. Mashima, K.; Kusano, K.-H.; Sato, N.; Matsumura, Y.-I.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Chem. Soc., Chem. Commun. 1991, 609.
47. Noboru, S.; Kumobayashi, H. (Takasago International Corp.). U.S. Patent US 5,324,870, 1994.
48. Lalonde M. F. (Hoffmann-La Roche AG). European Patent Appl. EP 0667350, 1995.
49. Cornils, B., Herrmann, W. A., Eds. Aqueous-phase Organometallic Catalysis; Wiley-VCH: Weinheim, Germany, 1998.
50. Foricher, J.; Heiser, B.; Schimd, R. (Hoffmann-La Roche AG). PCT Int. Appl. WO 9216535, 1992.
51. Foricher, J.; Heiser, B.; Schimd, R. (Hoffmann-La Roche AG). U.S. Patent US 5,274,-125, 1993.
52. Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Organic Syntheses; Vol. 76, p 6.
53. Sayo, N.; Zhang, X.; Oh, T.; Yoshida, A.; Hiratsuka-Shi, K.-K.; Yokozawa, T. (Takasago International Corp.). European Patent Appl. EP 0771812, 1997; U.S. Patent US 5,693,868, 1997.
54. Hunt, B. B.; Saunders, B. C. J. Chem. Soc. 1957, 2413.
55. Hays, H. R. J. Org. Chem. 1968, 33, 3690.
56. Goto, M.; Mano, M. (Takeda Chemical Industries). PCT Int. Appl. WO 03048174, 2003.
57. Goto, M.; Mano, M. (Takeda Chemical Industries). European Patent Appl. EP 1452537, 2004.
58. Sayo, N.; Zhang, X.; Omoto, T.; Yokozawa, T.; Yamasaki, T.; Kumobayashi, H. (Takasago International Corp.). European Patent Appl. EP 0754696, 1997.
59. Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033; Japanese Patent JP-A-6-263776.
60. Ding, H.; Kang, J.; Hanson, B. E.; Kohlpaintner, C. W. J. Mol. Catal. A 1997, 124, 21; PCT Int. Appl. WO 9739005, 1997.
61. Kohlpaintner, C. W.; Hanson, B. E.; Ding, H. U.S. Patent US 5,777,087, 1998.
62. Gladiali, S.; Dore, A.; Fabbri, D.; Medici, S.; Pirri, G.; Pulacchini, S. Eur. J. Org. Chem. 2000, 2861.
63. Betzemeier B.; Cavazzini, M.; Quici, S.; Knochel, P. Tetrahedron Lett. 2000, 41, 4343.
64. Jessop, P. G.; Ikaria, T.; Noyori, R. Chem. Rev. 1999, 99, 475.
65. Bayardon, J.; Cavazzini, M.; Maillard, D.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron: Asymmetry 2003, 14, 2215.
66. Nakamura, Y.; Takeuchi, S.; Zhang, S.; Okumura, K.; Ohgo, Y. Tetrahedron Lett. 2002, 43, 3053.
67. Dong, X.; Erkey, C. J. Mol. Catal. A 2004, 211, 73.
68. Jessop, P. G., Leitner, W., Eds. Chemical synthesis using supercritical fluids; Wiley-VCH: Weinheim, Germany, 1999.
69. Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065.
70. Leitner, W. Top Curr. Chem. 1999, 206, 107.
71. Xiao, J.; Neikens, S. C. A.; Jessop, P. G.; Ikariya, T.; Noyori, R. Tetrahedron Lett. 1996, 37, 2813.
72. Inoue, S.-I.; Osada, M.; Koyano, K.; Takaya, H.; Noyori, R. Chem. Lett. 1985, 1007.
73. Zhang, X.; Mashima, K.; Koyano, K. Noboru, S.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron Lett. 1991, 32, 7283.
74. Hori, Y.; Kumobayashi, H. (Takasago International Corp.). European Patent Appl. EP 0466405, 1992.
75. Andersen, N. G.; McDonald, R.; Keay, B. A. Tetrahedron: Asymmetry 2001, 12, 263.
76. Geldbach, T. J.; Pregosin, P. S.; Albinati, A. Organomettallics 2003, 22, 1443.
77. Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
78. Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. H.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Sogah, G. D. Y. J. Org. Chem. 1978, 43, 1930.
79. Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
80. Zhang, X. (The Penn State Research Foundation). PCT Int. Appl. WO 02/ 40491, 2002.
81. Cox, P. J. Tetrahedron Lett. 1992, 33, 2253.
82. Simonsen, K. B. J. Org. Chem. 1998, 63, 7536.
83. Kant, M.; Bischoff, S.; Siefken, R.; Gründemann, E.; Köckritz, A. Eur. J. Org. Chem. 2001, 477.
84. Kant, M.; Bischoff, S.; Siefken, R.; Gründemann, E.; Köckritz, A. DGMK Tagungsber. 2000, 239.
85. Kant, M.; Bischoff, S.; Siefken, R.; Köckritz, A. J. Mol. Catal. A 2001, 174, 119.
86. Köckritz, A. (Institut für Angewandte Chemie Berlin-Adlershof). German Patent DE 10062513, 2000.
87. (a) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
88. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
89. (c) Carlin, R. T.; Wilkes, J. S. In Advances in nonaqueous chemistry; Mamantov, G., Popov, A., Eds.; VCH: New York, 1994.
90. (d) Chauvin, Y.; Olivier-Bourbigou, H. CHEMTECH 1995, 25, 26.
91. (e) Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351.
92. (f) Olivier-Bourbigou, H. In Aqueous-phase organometallic catalysis: concept and applications; Cornils, B., Hermann, W. A., Eds.; Wiley-VCH: Wienheim, Geramny, 1998.
93. (g) Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catal. Today 2002, 74, 157.
94. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
95. (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
96. (c) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A 2002, 182-183, 419.
97. (a) Berger, A.; DeSouza, R. F.; Delgado, M. R.; Dupont, J. Tetrahedron: Asymmetry 2001, 12, 1825.
98. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G., Welton, T. Chem. Commun. 1999, 25.
99. Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumont, A. C.; Plaquevent, J. C. Tetrahedron: Asymmetry 2003, 14, 3081.
100. Ngo, H. L.; Hu, A.; Lin, W. Chem. Commun. 2003, 1912.
101. Hu, A.; Ngo, H. L.; Lin, W. J. Am. Chem. Soc. 2003, 125, 11490.
102. (a) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.
103. (b) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
104. (c) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510.
105. (d) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529.
106. (e) Ohkuma, T.; Koizumi, M.; Muñiz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508.
107. Kesanli, B.; Lin, W. Chem. Commun. 2004, 2284.
108. Berthod, M.; Saluzzo, C.; Mignani, G.; Lemaire, M. Tetrahedron: Asymmetry 2004, 15, 639.
109. Lemaire, M.; Saluzzo, C.; Berthod, M. (Rhodia/CNRS). French Patent FR 2849037, 2002.
110. Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano de Andrade, M.; Laffite, J. A. Tetrahedron: Asymmetry 1994, 5, 665.
111. Lamouille, T.; Saluzzo, C.; Ter Halle, R.; Le Guyader, F.; Lemaire, M.; Tetrahedron Lett. 2001, 42, 663.
112. Horväth, I. T. Acc. Chem. Res. 1998, 31, 641.
113. Barthel-Rosa, L. P.; Gladysz, J. A. Coord. Chem. Rev. 1999, 192, 587.
114. Hope, E. G.; Stuart, A. M. J. Fluorine Chem. 1999, 100, 75.
115. Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1988, 43, 207.
116. Berthod, M.; Mignani, G.; Lemaire, M. Tetrahedron: Asymmetry 2004, 15, 1121.
117. Kaupp, G. Angew. Chem. 1994, 33, 1452.
118. Boock, L.; Wu, B.; Lamarca, C.; Klein, M.; Paspek, S. CHEMTECH 1992, 719.
119. Hu, A.; Ngo, H. L.; Lin, W. Angew. Chem., Int. Ed. 2004, 43, 2501.
120. Maskill, H. The physical basis of organic chemistry; Oxford University Press: Oxford, U.K., 1985; pp 202-203.
121. Hu, A.; Ngo, H. L.; Lin, W. Org. Lett. 2004, 6, 2937.
122. (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.
123. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.
124. (c) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 12, 13529.
125. (d) Ohkuma, T.; Koizumi, M.; Muniz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508.
126. (e) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
127. (a) Sandoval, C. A.; Ohkuma, T.; Muniz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490.
128. (b) Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104.
129. (c) Abdur-Rashid, K.; Faatz, M.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2001, 123, 7473.
130. Kumobayashi, H. (Takasago Perfumery Co., Ltd.). European Patent Appl. EP 0235450, 1986.
131. Chan, A. S. C. (The Hong Kong Polytechnic University). U.S. Patent US 005,990,318, 1999.
132. Fan, Q. H.; Ren, C. Y.; Yeung, C. H.; Hu, W. H.; Chan, A. S. C. J. Am. Chem. Soc. 1999, 129, 7407.
133. Fan, Q. H.; Deng, G. J.; Chen, X. M.; Xie, W. C.; Jiang, D. Z.; Liu, D. S.; Chan A. S. C. J. Mol. Catal. A 2000, 159, 37.
134. Fan, Q. H.; Deng, G. J.; Lin, C. C.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1241.
135. Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689.
136. Fan, Q. H.; Chen, Y. M.; Chen, X. M.; Jiang, D. Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789.
137. Fan, Q. H.; Liu, G. H.; Deng, G. J.; Chen, X. M.; Chan, A. S. C. Tetrahedron Lett. 2001, 42, 9047.
138. Cornils, B.; Herrmann, W. A. Aqueous Phase Organometallic Catalysis, Concepts and Applications; VCH: Weinheim, New York, Basel, Cambridge, Tokyo, 1998.
139. Kuntz, E. G. CHEMTECH 1987, 17, 570.
140. Wan, K. T.; Davis, M. E. J. Chem. Soc., Chem. Commun. 1993, 1262.
141. Wan, K. T.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461.
142. Wan, K. T.; Davis, M. E. Nature 1994, 370, 449.
143. Wan, K. T.; Davis, M. E. J. Catal. 1995, 152, 25.
144. Kumobayashi, H. (Takasago International Corp.). European Patent EP 0544455, 1992.
145. Reichardt, C. Solvents and solvent effects in organic chemistry, 2nd ed.; VCH: Cambridge, New York, 1988; p 23.
146. Pradellok, W.; Kotas, A.; Walczyk, W.; Jedlinski, Z. PL 87054, 1976.
147. Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035.
148. Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. (Oxford Asymmetry Ltd.). PCT Int. Appl. WO 98/1220, 1998.
149. Bayston, D. J.; Fraser, J. L.; Ashton, M. R.; Baxter, A. D.; Polywka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137.
150. Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369.
151. Otomaru, Y.; Senda, T.; Hayashi, T. Org. Lett. 2004, 19, 3357.
152. Tamao, K.; Sayo, N. (Takasago International Corp.). European Patent Appl. EP 1041077, 2000.
153. Saluzzo, C.; Ter Halle, R.; Touchard, F.; Fache, F.; Schulz, E.; Lemaire, M. J. Organomet. Chem. 2000, 603, 30.
154. Lemaire, M.; Schulz, E.; Ter Halle, R.; Spagnol, M. (Rhodia/CNRS). PCT Int. Appl. WO 2000049028, 2000.
155. Ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. C. R. Acad. Sci., Ser. IIc 2000, 3, 553.
156. Veronese, F. M.; Caliceti, P.; Pastorino, A.; Schiavon, O.; Sartore, L.; Banci, L.; Monsu Scolaro, L. J. Controlled Release 1989, 10, 145.
157. Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett. 1991, 32, 4163.
158. Guerreiro, P.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Dellis, P. Tetrahedron Lett. 2001, 42, 3423.
159. Dellis, P.; Gueirrero, P.; Genet, J. P. (Fournier Industrie Santé). French Patent FR 2801886, 2001.
160. Ngo, H. L.; Hu, A.; Lin, W. Chem. Commun. 2003, 1912.
161. Bhattacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmit, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1997, 3609.
162. (a) Chen, W.; Xiao, J. Tetrahedron Lett. 2000, 41, 3697.
163. (b) Chen, W.; Xiao, J. Org. Lett. 2000, 2, 2675.
164. (c) Chen, W.; Xu, L.; Xiao, J. Tetrahedron Lett. 2001, 41, 4275.
165. Birdsall, D. J.; Hope, E. G.; Stuart, A. M.; Chen, W.; Hu, Y.; Xiao, J. Tetrahedron Lett. 2001, 42, 8551.
166. Dumont, W.; Poulin, J. C.; Dang, T. P.; Kagan, H. B. J. Am. Chem. Soc. 1973, 95, 8295.
167. Takaishi, N.; Imai, H.; Bertelo, C. A.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 264.
168. Matsuda, T.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 268.
169. Deschenaux, R.; Stille, J. K. J. Org. Chem. 1985, 50, 2299.
170. Stille, J. K.; Parrinello, G. J. Mol. Catal. 1983, 21, 203.
171. Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 3003.
172. Canali, L.; Karjalainen, J. K.; Sherrington, D. C.; Hormi, O. Chem. Commun. 1997, 123.
173. Blaser, H. U.; Jalett, H. P.; Spindler, F. J. Mol. Catal. A 1996, 107, 85.
174. Saluzzo, C.; Lamouille, T.; Le Guyader, F.; Lemaire, M. Tetrahedron: Asymmetry 2002, 13, 1141.
175. Saluzzo, C.; Lamouille, T.; Hérault, D.; Lemaire, M. Bioorg. Med. Chem. Lett. 2002, 12, 1841.
176. Saluzzo, C.; Lemaire, M. Adv. Synth. Catal. 2002, 344, 915.
177. Ter Halle, R.; Schulz, E.; Spagnol, M.; Lemaire, M. Tetrahedron Lett. 2000, 41, 3323.
178. Saluzzo, C.; ter Halle, R.; Touchard, F.; Fache, F.; Schulz, E.; Lemaire, M. J. Organomet. Chem. 2000, 603, 30.
179. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.
180. Yu, H.-B.; Hu, Q.-S.; Pu, L. Tetrahedron Lett. 2000, 41, 1681.
181. Yu, H.-B.; Hu, Q.-S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500.
182. Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 2000, 41, 57.
183. Studer, A.; Jeger, P.; Wipf, C.-W.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
184. Nakamura, Y.; Takeuchi, S.; Zhang, S.; Okumura, K.; Ohgo, Y. Tetrahedron Lett. 2002, 43, 353.
185. Nakamura, Y.; Takeuchi, S.; Ohgo, Y. J. Fluorine Chem. 2003, 120, 121.
186. Lamouille, T. Nouveaux catalyseurs hétérogènes dérivés du BINAP: Applications en catalyse biphasique; Th. Chimie: Lyon, 2001; 125.
187. Pugin, B. J. Mol. Catal. A 1996, 107, 273.
188. Pugin, B.; Müller, M. Stud. Surf Sci. Catal. 1993, 78, 107.
189. Cai, D. W. (Merck & Co., Inc.). Japanese Patent JP 08311090, 1996;
190. U.S. Patent US 6,333,435, 2001.
191. Che, D.; Andersen, N. G.; Lau, S. Y. W.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 2000, 11, 1919.
192. Noji, M.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 35, 7983.
193. Shan, Z.; Xiong, Y.; Zhao, D. Tetrahedron 1999, 55, 3893.
194. Ager, D. J.; East, M. B.; Eisenstadt, A.; Laneman, S. A. J. Chem. Soc., Chem. Commun. 1997, 2359.
195. Yokozawa, T.; Salto, K. (Takasago International Corp.). European Patent Appl. EP1371655, 2003.