A new class of versatile chiral-bridged atropisomeric diphosphine ligands: Remarkably efficient ligand syntheses and their applications in highly enantioselective hydrogenation reactions

Journal of the American Chemical Society

Volumn 128, Issue 17, 2006, Pages 5955-5965

  Qiu, Liqin ^a   Kwong, Fuk Yee ^a   Wu, Jing ^a   Lam, Wai Har ^a   Chan, Shusun ^a   Yu, Wing Yiu ^a   Li, Yue Ming ^a   Guo, Rongwei ^a   Zhou, Zhongyuan ^a   Chan, Albert S C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; HYDROGENATION; REACTION KINETICS;

DIHEDRAL ANGLE EFFECTS; ENANTIOSELECTIVE HYDROGENATION REACTIONS; HETEROAROMATIC COMPOUNDS; LIGAND SCAFFOLD;

AROMATIC COMPOUNDS;

LIGAND; PHOSPHINE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; COMPLEX FORMATION; COUPLING FACTOR; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

HYDROGEN; LIGANDS; PHOSPHINES; STEREOISOMERISM;

EID: 33646677236     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0602694     Document Type: Article

References (130)

1. For some reviews, see: (a) Kitamura, M.; Noyori, R. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, pp 116-199.
2. (b) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. (c) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley: New York, 2000.
4. (d) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vol. 1.
5. (e) Brunner, H. In Topics in Stereochemistry; Eliel, E., Wilen, S. H., Eds.; Wiley: New York, 1988; Vol. 18, p 129.
6. (f) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
7. (g) Lin, G.-Q.; Li, Y.-M.; Chan, A. S. C. Principles and Applications of Asymmetric Synthesis; Wiley: New York, 2001.
8. (h) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
9. (i) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
10. (a) Pai, C.-C.; Lin, C.-W.; Lin, C.-C.; Chen, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 2000, 122, 11513.
11. (b) Pai, C.-C.; Chan, A. S. C. U.S. Patent 5,886,182, 1999.
12. (c) Wu, J.; Ji, J.-X.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 3570.
13. (d) Wu, J.; Chen, H.; Zhou Z.-Y.; Yeung C.-H.; Chan, A. S. C. Synlett 2001, 1050.
14. (e) Wu, J.; Chen, H.; Kwok W.-K.; Lam K.-H.; Zhou Z.-Y.; Yeung C.-H.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 1539.
15. (f) Kwong, F. Y.; Li, Y.-M.; Lam, W. H.; Qiu, L.; Lee, H. W.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Eur. J. 2005, 11, 3872.
16. (a) Pai, C.-C.; Li, Y.-M.; Zhou, Z.-Y.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 2789.
17. (b) Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Fr. Patent 2,830,254, 2001.
18. (c) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Eur. J. Org. Chem. 2003, 1931.
19. (d) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Tetrahedron Lett. 2003, 44, 823.
20. (e) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Angew. Chem., Int. Ed. 2004, 43, 320.
21. (f) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799.
22. (g) Genêt, J.-P. Acc. Chem. Res. 2003, 36, 908-918.
23. (a) Benincori, T.; Brenna, E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E. J. Chem. Soc., Chem. Commun. 1995, 685.
24. (b) Benincori, T.; Brenna E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244.
25. (c) Benincori, T.; Brenna E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T.; Zotti, G. J. Organomet. Chem. 1997, 529, 445.
26. (d) Tietze, L. F.; Thede, K.; Schimpf, R.; Sannicolo, F. Chem. Commun. 2000, 583.
27. (e) Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolo, F. J. Org. Chem. 2000, 65, 2043.
28. (a) Saito, T.; Yokozawa, T.; Zhang, X. Y.; Sayo, N. U.S. Patent 5,872,273, 1999.
29. (b) Saito, T.; Yokozawa, T.; Ishizaki T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
30. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249.
31. Gelpke, A. E. S.; Kooijman, H.; Spek, A. L.; Hiemstra, H. Chem. Eur. J. 1999, 5, 2472.
32. (a) Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño de Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665.
33. (b) Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño de Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675.
34. (c) Tranchier, J.-P.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Tong, S.; Cohen, T. Tetrahedron Lett. 1997, 38, 2951.
35. (d) Blanc, D.; Henry, J.-C.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Tetrahedron Lett. 1997, 38, 6603.
36. (a) Miyashita, A.; Yasuda, H.; Takaya, H.; Toriumi K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
37. (b) Noyori, R., Takaya, H. Acc. Chem. Res. 1990, 23, 345.
38. (c) Noyori, R. Chem. Soc. Rev. 1989, 18, 187.
39. (a) Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H. J. Helv. Chim. Acta 1988, 71, 897.
40. (b) Schmid, R.; Foricher, J.; Cereghetti, M.; Schonholzer, P. Helv. Chim. Acta 1991, 74, 370.
41. (c) Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Muller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131.
42. (a) Dierkes, P.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1999, 1519.
43. (b) van der Veen, L. A.; Boele, M. D. K.; Bregman, F. R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.; Schenk, H.; Bo, C. J. Am. Chem. Soc. 1998, 120, 11616.
44. (c) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3081.
45. (d) Meessen P.; Vogt, D.; Keim, W. J. Organomet. Chem. 1998, 551, 165.
46. (e) Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535.
47. (a) Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223.
48. (b) Wu, S.; Wang, W.; Tang, W.; Lin, M.; Zhang, X. Org. Lett. 2002, 4, 4495.
49. For some reviews, see; (a) Meyers, A. I.; Nelson, T. D.; Moorlag, H.; Rawson, D. J.; Merier, A. Tetrahedron 2004, 60, 4459.
50. (b) Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
51. For some examples, see: (c) Harada, T.; Ueda, S.; Yoshida, T.; Inoue, A.; Takeuchi, M.; Ogawa, N.; Oku. A. J. Org. Chem. 1994, 59, 7575.
52. (d) Tuyet, T. M. T.; Harada, T.; Hashimoto, K.; Hatsuda, M.; Oku, A. J. Org. Chem. 2000, 65, 1335.
53. (e) Lin, G.-Q.; Zhong, M. Tetrahedron Lett. 1997, 38, 1087.
54. (f) Itoh, T.; Chika, J.-i. J. Org. Chem. 1995, 60, 4968.
55. (g) Lipshutz, B. H.; Kayser, F.; Liu, Z.-P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1842.
56. (h) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753.
57. (i) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259.
58. (j) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
59. (k) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
60. (l) Rawai, V. H.; Florjancic, A. S.; Singh, S. P. Tetrahedron Lett. 1994, 35, 8985.
61. (m) Ku, Y.-Y.; Grieme, T.; Raje, P.; Sharma, P.; King, S. A.; Morton, H. E. J. Am. Chem. Soc. 2002, 124, 4282.
62. (n) Miyano, S.; Fukushima, H.; Handa, S.; Ito, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 3249.
63. (o) Nelson, S. G.; Hilfiker, M. A. Org. Lett. 1999, 1, 1379.
64. (p) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. J. Am. Chem. Soc. 2002, 124, 1354.
65. (q) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 67, 1375.
66. (r) Vorogushin, A. V.; Wulff, W. D.; Hansen, H.-J. J. Am. Chem. Soc. 2002, 124, 6512.
67. (s) Michaud, G.; Bulliard, M.; Ricard, L.; Genêt, J.-P.; Marinetti, A. Chem. Eur. J. 2002, 8, 3327.
68. (t) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051.
69. (u) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
70. Qiu, L.; Qi, J.; Pai, C.-C.; Chan, S.; Zhou, Z.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2002, 4, 4599.
71. Qiu, L.; Wu, J.; Chan, S.; Au-Yeung, T. T.-L.; Ji, J.-X.; Guo, R.; Pai, C.-C.; Zhou, Z.; Li, X.; Fan, Q.-H.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5815.
72. (a) Evans, D. A.; Dinsmore, C. J. Tetrahedron Lett. 1993, 34, 6029.
73. (b) Feldman, K. S., Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc. 1994, 116, 1742.
74. (c) Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357.
75. (d) Maitra, U.; Bandyopadhyay, A. K. Tetrahedron Lett. 1995, 36, 3749.
76. Qiu, L.; Qi, J.; Ji, J.-X. Acta Crystallogr. 2003, C59, o33.
77. Chem 3D Ultra, 7.0.0 Version; Cambridge Scientific Computing, Inc., 2001.
78. (a) Chiba T.; Miyashita, A.; Nohira, H.; Takaya, H. Tetrahedron Lett. 1993, 34, 2351.
79. (b) 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. Org. Chem. 1994, 59, 3064.
80. (c) Hapiot, F.; Agbossou, F.; Mortreux, A. Tetrahedron: Asymmetry 1995, 6, 11.
81. (d) Carpentier, J.-F.; Mortreux, A. Tetrahedron: Asymmetry 1997, 8, 1083.
82. (e) Burk, M. J.; Pizzano, A.; Martin, J. A. Organometallics 2000, 19, 250.
83. (f) Boaz, N. W.; Debenham, S. D.; Mackenzie, E. B.; Large, S. E. Org. Lett. 2002, 4, 2421.
84. (g) Boaz, N. W.; Mackenzie, E. B.; Debenham, S. D.; Large, S. E.; Ponasik, J. A. J. Org. Chem. 2005, 70, 1872.
85. For some reviews, see: (a) Ager, D. J.; Laneman S. A. Tetrahedron: Asymmetry 1997, 8, 3327.
86. (b) Kwong, F. Y.; Qiu, L.; Lam, W. H.; Chan, A. S. C. In Advances in Organic Synthesis; Jenner, G., Ed.; Bentham: Pakistan, 2005; Vol. 1, pp 261-299.
87. For some examples, see: (c) Hu, A. Ngo, H. L.; Lin, W. Angew. Chem., Int. Ed. 2004, 43, 2501.
88. (d) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth., 1993, 71, 1.
89. (a) Harrington, P. J.; Lodewijk, E. Org. Process Res. Dev., 1997, 1, 72.
90. (b) Chan, A. S. C. U.S. Patent 4,994,607. 1991.
91. (c) Chan, A. S. C. U.S. Patent 5,144,050. 1992.
92. (d) Rieu, J.-P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095.
93. (e) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510.
94. Juaristi, E., Ed. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997.
95. (a) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
96. (b) Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159.
97. (c) Lee, S.-g.; Zhang, Y. J. Org. Lett. 2002, 4, 2429.
98. (d) Yasutake, M.; Gridnev, I. D.; Higashi, N.; Imamoto, T. Org. Lett. 2001, 3, 1701.
99. (e) Heller, D.; Holz, J.; Drexler, H.-J.; Lang, J.; Drauz, K.; Krimmer, H.-P.; Börner, A. J. Org. Chem. 2001, 66, 6816.
100. (f) Zhu, G.; Chen, Z.; Zhang, X. J. Org. Chem. 1999, 64, 6907.
101. (g) Furukawa, M.; Okawara, T.; Noguchi, Y.; Terawaki, Y. Chem. Pharm. Bull. 1979, 27, 2223.
102. (h) Achiwa, K.; Soga, T. Tetrahedron Lett. 1978, 19, 1119.
103. (i) Hu, X.-P.; Zheng, Z. Org. Lett. 2005, 7, 419.
104. (j) Fu, Y.; Guo, X.-X.; Zhu, S.-F.; Hu, A.-G.; Xie, J.-H.; Zhou, Q.-L. J. Org. Chem. 2004, 69, 4648.
105. (a) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543.
106. (b) Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952.
107. (c) Tang, W.; Wu, S.; Zhang, X. Am. Chem. Soc. 2003, 125, 9570.
108. (d) Wu, J., Chen, X., Guo, R., Yeung, C.-H.; Chan, A. S. C. J. Org. Chem. 2003, 68, 2490.
109. (a) Keay, J. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, pp 579-601.
110. (b) Barton, D. H. R.; Nakanishi, K.; Meth-Cohn, O., Eds. Comprehensive Natural Products Chemistry; Elsevier: Oxford, 1999; Vol. 1-9.
111. For early examples, see: (a) Spindler, F.; Pugin, B.; Blaser, H.-U. Angew. Chem., Int. Ed. Engl. 1990, 29, 558.
112. (b) Bakos, J.; Toth, I.; Heil, B.; Szalontai, G.; Parkanyi, L.; Fulop, V. J. Organomet. Chem. 1989, 370, 263.
113. (c) Kang, G.-J.; Cullen, W. R.; Fryzuk, M. D.; James, B. R.; Kutney, J. P. J. Chem. Soc., Chem. Commun. 1988, 1466.
114. (d) Vastag, S.; Bakos, J.; Toros, S.; Takach, N. E.; King, R. B.; Heil, B.; Marko, L. J. Mol. Catal. 1984, 22, 283.
115. (e) Ng Cheong Chan, Y.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400.
116. (f) Langlois, N.; Dang, T.-P.; Kagan, H. B. Tetrahedron Lett. 1973, 4865.
117. (g) Lensink, C.; de Vries, J. G. Tetrahedron: Asymmetry 1992, 3, 235.
118. (h) Morimoto, T.; Nakajima, N.; Achiwa, K. Synlett 1995, 748.
119. (i) Sablong, R.; Osborn, J. A. Tetrahedron Lett. 1996, 37, 4937.
120. (j) Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887.
121. (k) Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
122. (l) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415.
123. (m) Bianchini, C.; Barbaro, P.; Scapacci, G.; Farnetti, E.; Graziani, M. Organometallics 1998, 17, 3308.
124. For recent examples, see: (a) Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.
125. (b) Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Adv. Synth. Catal. 2004, 346, 909.
126. (c) Cobley, C. J.; Henschke, J. P. Adv. Synth. Catal. 2003, 345, 195.
127. (d) Giernoth, R.; Krumm, M. S. Adv. Synth. Catal. 2004, 346, 989.
128. (e) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
129. (f) Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, Y. Org. Lett. 2004, 6, 2213.
130. (g) Blaser, H.-U.; Buser, H.-P.; Häusel, R.; Jalett, H.-P.; Spindler, F. J. Organomet. Chem. 2001, 621, 34.