Resolutions at large scale: Case studies

Handbook of Chiral Chemicals

Volumn , Issue , 2005, Pages 75-95

  Liu, Weiguo ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

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EID: 85130556963     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (136)

1. Jacques, J., Collet, A., Wilen, S. Enantiomers, Racemates, and Resolutions, Wiley: New York, 1981.
2. Bayley, C. R., Vaidya, N. A. in Chirality in Industry, Collins, A. N., Sheldrake, G. N., Crosby, J., Eds., Wiley: New York, 1992, p. 71.
3. CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation, Kozma, D., Ed., CRC Press: Boca Raton, 2002.
4. Kinbara, K., Tagawa, Y., Saigo, K. Tetrahedron: Asymmetry 2001, 12, 2927.
5. Reinhold, D. F., Firestone, R. A., Gaines, W. A., Chemerda, J. M., Sletzinger, M. J. Org. Chem. 1968, 33, 1209.
6. Amiard, G. Experientia 1959, 15, 1.
7. Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, Inc.: New York, 1993.
8. Wilen, S. H. Tables of Resolving Agents, University of Notre Dame: Notre Dame, IN, 1972.
9. Newman, P. Optical Resolution Procedures, Resolution Information Center, Manhattan College: New York, 1981.
10. Eames, J. Angew. Chem., Int. Ed. 2000, 39, 885.
11. Johnson, D. W., Singleton, D. A. J. Am. Chem. Soc. 1999, 121, 9307.
12. Harrison, I. T., Lewis, B., Nelson, P., Rooks, W., Roszkowski, A., Tomolonis, A., Fried, J. H. J. Med. Chem. 1970, 13, 203.
13. Harrington, P. J., Lodewijk, E. Org. Proc. Res. Dev. 1997, 1, 72.
14. Holton, P. G. U.S. Pat. 4,246,193, 1981.
15. Felder, E., San Vitale, R., Pitre, D., Zutter, H. U.S. Pat. 4,246,164, 1981.
16. Sonawane, H. R., Bellur, N. S., Ahuja, J. R., Kulkarni, D. G. Tetrahedron: Asymmetry 1992, 3, 163.
17. Giordano, C., Castaldi, G., Cavicchioli, S., Villa, M. Tetrahedron 1998, 45, 4243.
18. Ohta, T., Takaya, H., Kitamura, M., Nagai, K., Noyori, R. J. Org. Chem. 1987, 52, 3174.
19. Chan, A. S. C., Laneman, S. A. U.S. Pat. 5,202,473, 1993.
20. Chan, A. S. C., Laneman, S. A. U.S. Pat. 5,144,050, 1992.
21. Chan, A. S. C. Chemtech. 1993, 23, 46.
22. Stille, J. K., Su, H., Brechot, P., Parinello, G., Hegedus, L. S. Organometallics 1991, 10, 1183.
23. Hiyama, T., Wakasa, N., Kusumoto, T. Synlett 1991, 569.
24. Alper, H., Hamel, N. J. Am. Chem. Soc. 1990, 112, 2803.
25. RajanBabu, T. V., Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265.
26. Piccolo, O., Azzena, U., Melloni, G., Delogu, G., Valoti, E. J. Org. Chem. 1991, 56, 183.
27. Piccolo, O., Speafico, F., Visentin, G. J. Org. Chem. 1985, 50, 1946.
28. Reid, A. J., Phillips, G. T., Marx, A. F., Desmet, M. J. Eur. Pat. 0 338 645-A, 1989.
29. Phillips, G. T., Robertson, B. W., Watts, P. D., Matcham, G. W. J., Bertola, M. A., Marx, A. F., Koger, H. S. Eur. Pat. Appl. 205 215, 1986.
30. Nicholson, J. S., Adams, S. S. U.K. Pat. 971 700, 1964.
31. Nicholson, J. S., Adams, S. S. U.S. Pat. 3,228,831, 1966.
32. Adams, S. S., Bresloff, P., Mason, G. Pharm. Pharmacol. 1967, 28, 256.
33. Adams, S. S., Cliffe, E. E., Lessel, B., Nicholson, J. S. J. Pharm. Sci. 1967, 56, 1686.
34. Wechter, W. J., Loughhead, D. G., Reischer, R. J., Van Giessen, G. J., Kaiser, D. G. Biochem. Biophys. Res. Commun. 1974, 61, 833.
35. Sunshine, A., Laska, E. M. U.S. Pat. 4,851,444, 1989.
36. Chan, A. S. C. U.S. Pat. 4,994,607, 1991.
37. Fowler, R., Connor, H., Bachl, R. A. Chemtech 1976, 722.
38. Rieu, J.-P., Boucherle, A., Cousse, H., Mouzin, G. Tetrahedron 1986, 42, 4095.
39. Shimizu, I., Matsumura, Y., Tokumoto, Y., Uchida, K. U.S. Pat. 4,694,100, 1987.
40. Shimizu, I., Matsumaura, Y., Tokumoto, Y., Uchida, K. U.S. Pat. 5,097,061, 1992.
41. Tokumoto, Y., Shimizu, I., Inooue, S. U.S. Pat. 5,166,419, 1992.
42. Boots Pure Drug Co. Fr. Pat. 1,545,270, 1968.
43. Boots Pure Drug Co. Chem. Mkt. Rep. 1993, 20.
44. Boots Pure Drug Co. Chem. Mkt. Rep. 1993, 41.
45. Tung, H.-H., Waterson, S., Reynolds, S. D. U.S. Pat. 4,994,604, 1991.
46. Trace, T. L. U.S. Pat. 5,278,338, 1994.
47. Larsen, R. D., Reider, P. U.S. Pat. 4,946,997, 1990.
48. Lin, R. W. U.S. Pat. 5,278,334, 1994.
49. Manimaran, T., Impastato, F. J. U.S. Pat. 5,015,764, 1991.
50. Nohira, H. U.S. Pat. 5,321,154, 1994.
51. Dwivedi, S. K., Sattari, S., Jamali, F., Mitchell, A. G. Int. J. Pharm. 1992, 87, 95.
52. Manimaran, T., Stahly, P. G. Tetrahedron: Asymmetry 1993, 4, 1949.
53. Manimaram, T., Stahly, P. G. U.S. Pat. 5,248,813, 1993.
54. Matson, S. L. U.S. Pat. 4,800,162, 1989.
55. Wald, S. A., Matson, S. L., Zepp, C. M., Dodds, D. R. U.S. Pat. 5,057,427, 1991.
56. Cobbs, C. S., Barton, M. J., Peng, L., Goswani, A., Malick, A. P., Hamman, J. P., Calton, G. J. U.S. Pat. 5,108,916, 1992.
57. Goswani, A. U.S. Pat. 5,175,100, 1992.
58. Bertola, M. A., Marx, A. F., Koger, H. S., Quax, W. J., Van der Laken, C. J., Phillips, G. T., Robertson, B. W., Watts, P. O. U.S. Pat. 4,886,750, 1989.
59. Bertola, M. A., De Smet, M. J., Marx, A. F., Phillips, G. T. U.S. Pat. 5,108,917, 1992.
60. Sih, C. J. Eur. Pat. Appl. 227 078, 1986.
61. Yamada, S., Hongo, C., Yoshioka, R., Chibata, I. J. Org. Chem. 1983, 48, 843.
62. Shiraiwa, T., Shinjo, K., Kurokawa, H. Chem. Lett. 1989, 1413.
63. Shiraiwa, T., Shinjo, K., Kurokawa, H. Bull. Chem. Soc., Jpn. 1991, 64, 3251.
64. Huang, T., Qian, X. Shipin Yu Fajiao Gongye 1987, 6, 98.
65. Kolb, H. C., VanNieuwenhze, M. S., Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
66. Jacobsen, E. N. in Comprehensive Organometallic Chemistry II, Wilkinson, G., Stone, F. G. A., Abel, E. W., Hegedus, L. S., Eds., Pergamon: New York, 1995, Vol. 12, Chapter 11.1.
67. Aggarwal, V. K., Ford, J. G., Thompson, A., Jones, R. V. H., Standen, M. J. Am. Chem. Soc. 1996, 118, 7004.
68. Sinigalia, R., Michelin, R. A., Pinna, F., Strukul, G. Organometallics 1987, 6, 728.
69. Tokunaga, M., Larrow, J. F., Kakiuchi, F., Jacobsen, E. N. Science 1997, 277, 936.
70. Sato, K., Aoki, M., Ogawa, M., Hashimoto, T., Noyori, R. J. Org. Chem. 1996, 61, 8310.
71. Pettman, R. B. Chemspec Europe BACS Symposium 1997, Manchester, 37.
72. Aouni, L., Hemberger, K. E., Jasmin, S., Kabir, H, Larrow, J. F., Le-Fur, I., Morel, P., Schlama, T. In Asymmetric Catalysis on Industrial Scale, Blaser, H. U., Schmidt, E., Eds., Wiley-VCH: Weinheim, 2004, p. 165.
73. Sticher, H., Faber, K. Synthesis, 1997, 1.
74. Asymmetric Catalysis on Industrial Scale, Blaser, H. U., Schmidt, E., Eds., Wiley-VCH, Weinheim, 2004.
75. Paul, P. K. C., Sukumar, M., Blasio, B. D., Pavone, V., Pedone, C., Balaram, P. J. Am. Chem. Soc. 1986, 108, 6363.
76. Bardi, R., Piazzesi, A. M., Toniolo, C., Sukumar, M., Balaram, P. Biopolymers 1986, 25, 1635.
77. Mutter, M. Angew. Chem. 1985, 97, 639.
78. Barone, V., Lelj, F., Bavoso, A., Blasio, B. D., Grimaldi, P., Pavone, V., Pedone, C. Biopolymers 1985, 24, 1759.
79. Khosla, M. C., Stackiwiak, K., Smeby, R. R., Bumpus, F. M., Piriou, F., Lintner, K., Fermandijan, S. Proc. Natl. Acad. Sci., USA 1981, 78, 757.
80. Turk, J., Panse, G. T., Marshall, G. R. J. Org. Chem. 1975, 40, 953.
81. Deeks, T., Crooks, T. P. A., Waigh, R. D. J. Med. Chem. 1983, 26, 762.
82. Christensen, H. N., Handlogten, M. E., Vadgama, J. V., de la Cuesta, E., Ballesteros, P., Trigo, G. C., Avendano, C. J. Med. Chem. 1983, 26, 1374.
83. Zembower, D. E., Gilbert, J. A., Ames, M. M. J. Med. Chem. 1993, 36, 305.
84. Kollonitsch, J., Patchett, A. A., Marburg, S., Maycock, A. L., Perkins, L. M., Doldouras, G. A., Duggan, D. E., Aster, S. D. Nature 1978, 274, 906.
85. Bhattacharjee, M. K., Snell, E. E. J. Biol. Chem. 1990, 265, 6664.
86. Schirlin, D., Gerhart, F., Hornsperger, J. M., Hamon, M., Wagner, J., Jung, M. J. J. Med. Chem. 1988, 31, 30.
87. Coppola, G. M., Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids, Wiley: New York, 1987.
88. Evans, D. A. in Asymmetric Synthesis, Morrison, J. D., Ed., Academic Press: Orlando, 1984, Vol. 3, p. 1.
89. Mzengeza, S., Yang, C. M., Whitney, R. A. J. Am. Chem. Soc. 1987, 109, 276.
90. Knudson, C. G., Palkowitz, A. D., Rappaport, H. J. Org. Chem. 1985, 50, 325.
91. Lubell, W. D., Rappaport, H. J. Am. Chem. Soc. 1987, 109, 236.
92. Williams, R. M., Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276.
93. Schollkopf, U. Pure Appl. Chem. 1983, 55, 1799.
94. Schollkopf, U., Busse, U., Lonsky, R., Hinrichs, R. Liebigs Ann. Chem. 1986, 2150.
95. Seebach, D., Boes, M., Naef, R., Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
96. Seebach, D., Aebi, J. D., Naef, R., Weber, T. Helv. Chim. Acta 1985, 65, 144.
97. O'Donnell, M. J., Bennett, W. D., Bruder, W. A., Jacobson, W. N., Knuth, K., LeClef, B., Polt, R. L., Bordwell, F. G., Mrozack, S. R., Cripe, T. A. J. Am. Chem. Soc. 1988, 110, 8520.
98. Kolb, M., Barth, J. Angew. Chem. 1980, 92, 753.
99. Goerg, G. I., Guan, X., Kant, J. Tetrahedron Lett. 1988, 29, 403.
100. Obrecht, D., Spiegler, C., Schönholzer, P., Müller, K., Heimgartner, H., Stierli, F. Helv. Chim. Acta 1992, 75, 1666.
101. Bosch, R., Brückner, H., Jung, G., Winter, W. Tetrahedron 1982, 38, 3579.
102. Anantharamaiah, G. M., Roeske, R. W. Tetrahedron Lett. 1982, 23, 3335.
103. Berger, A., Smolarsky, M., Kurn, N., Bosshard, H. R. J. Org. Chem. 1973, 38, 457.
104. Kamphuis, J., Boesten, W. H. J., Broxterman, Q. B., Hermes, H. F. M., Meijer, E. M., Schoemaker, H. E. in Adv. Biochem. Engineering Biotechnol., Flechter, A., Ed., Springer-Verlag: Berlin, 1990, Vol. 42.
105. Schollkopf, U., Hartwig, W., Groth, U., Westphalen, K.-O. Liebigs Ann. Chem. 1981, 696.
106. Gross, C., Syldatk, C., Mackowiak, V., Wagner, F. J. Biotechnology 1990, 14, 363.
107. Chevalier, P., Roy, D., Morin, A. Appl. Microbiol. Biotechnol. 1989, 30, 482.
108. West, T. P. Arch. Microbiol. 1991, 156, 513.
109. Shimizu, S., Shimada, H., Takahashi, S., Ohashi, T., Tani, Y., Yamada, H. Agric. Biol. Chem. 1980, 44, 2233.
110. Syldatk, C., Wagner, F. Food Biotechnol. 1990, 4, 87.
111. Runser, S., Chinski, N., Ohleyer, E. Appl. Microbiol. Biotechnol. 1990, 33, 382.
112. Nishida, Y., Nakamicho, K., Nabe, K., Tosa, T. Enzyme Micro. Technol. 1987, 9, 721.
113. Chenault, H. K., Dahmer, J., Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354.
114. Keller, J. W., Hamilton, B. J. Tetrahedron Lett. 1986, 27, 1249.
115. Kruizinga, W. H., Bolster, J., Kellogg, R. M., Kamphuis, J., Boesten, W. H. J., Meijer, E. M., Schoemaker, H. E. J. Org. Chem. 1988, 53, 1826.
116. Schoemaker, H. E., Boesten, W. H. J., Kaptein, B., Hermes, H. F. M., Sonke, T., Broxterman, Q. B., van den Tweel, W. J. J., Kamphuis, J. Pure Appl. Chem. 1992, 64, 1171.
117. Stein, G. A., Bronner, H. A., Pfister, K. J. Am. Chem. Soc. 1955, 77, 700.
118. Ware, E. Chem. Rev. 1950, 46, 403.
119. Yee, C., Blythe, T. A., McNabb, T. J., Walts, A. E. J. Org. Chem. 1992, 57, 3525.
120. Toone, E. J., Jones, J. B. Tetrahedron: Asymmetry 1991, 2, 201.
121. Lam, L. K. P., Brown, C. M., Jeso, B. D., Lym, L., Toone, E. J., Jones, J. B. J. Am. Chem. Soc. 1988, 110, 4409.
122. Chen, C. S., Fujimoto, Y., Girdaukas, G., Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
123. Liu, W., Ray, P., Beneza, S. A. J. Chem. Soc., Perkin Trans. I 1995, 553.
124. Roth, H. J., Fenner, H. Arzneistoffe-Pharmazeutische Chemie III, Georg Thieme: Stuttgart, 1988.
125. Patchett, A. A. Nature 1980, 288, 280.
126. Dürekheimer, W., Blumbach, J., Lattreil, R., Scheunemann, K. H. Angew. Chem. 1985, 97, 183.
127. Kamphuis, J., Boesten, W. H. J., Schoemaker, H. E., Meijer, E. M. In Conference Proceedings on Pharmaceutical Ingredients and Intermediates, Reuben, B. G., Ed., Expoconsult: Maarsen, 1991, p. 28.
128. Williams, R. M. Synthesis of Optically Active a-Amino Acids, Pergamon Press: Oxford, 1989.
129. Morin, A., Hummel, W., Kula, M.-R. Appl. Microbiol. Biotechnol. 1986, 25, 91.
130. Morin, A., Touzel, J.-P., Lafond, A., Leblanc, D. Appl. Microbiol. Biotechnol. 1991, 35, 536.
131. Olivieri, R., Fascetti, E., Angelini, L., Degen, L. Enzyme Microb. Technol. 1979, 1, 201.
132. Olivieri, R., Fascetti, E., Angelini, L., Degen, L. Biotechnol. Bioeng. 1981, 23, 2173.
133. Bucherer, H. T., Steiner, W. J. Prakt. Chem. 1934, 140, 291.
134. Takahashi, S., Ohashi, T., Kii, Y., Kumagai, H., Yamada, H. J. Ferment. Technol. 1979, 57, 328.
135. Battilott, M., Barberini, U. J. Mol. Catal. 1988, 43, 343.
136. Keil, O., Schneider, M. P., Rasor, J. P. Tetrahedron: Asymmetry 1995, 6, 1257.