Resolution of enantiomers of chiral drugs

New Trends in Synthetic Medicinal Chemistry

Volumn , Issue , 2008, Pages 139-173

  Blaschke, Gottfried ^a   Chankvetadze, Bezhan ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b TBILISI STATE UNIVERSITY   (Georgia)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL DRUGS; RESOLUTION OF ENANTIOMERS;

ENANTIOMERS;

EID: 84863451752     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527613403.ch6     Document Type: Chapter

References (185)

1. Mason, S. Trends Pharm Sci. 1, 20-23 (1986).
2. Pasteur, L. In: Richardson, G.M. (ed.) On The Asymmetry of Naturally Occurring Organic Compounds, The Foundations of Stereo Chemistry: Memories by Pasteur, Van't Hoff, Le Bel, and Wislicenus. American Book Co.: New York, 1901, pp. 1-33.
3. Ariens, E.J., Soudijn, W., and Timmermans, P.B.M.W.W. Stereochemistry and Biological Activity of Drugs. Blackwell Scientific Publications: Oxford, UK 1983.
4. Wainer, I.W., and Drayer, D.E. Drug Stereochemistry (Analytical Methods and Pharmacology) Marcel Dekker, Inc.: New York, Basel, 1988.
5. Collins, A.N., Sheldrake, G.N., and Crosby, J. (eds) Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds John Wiley & Sons: Chichester, 1992.
6. Crossley, R. Chirality and The Biological Activity of Drugs CRC Press, Inc.: Boca Raton, 1995.
7. Pifferi, G., and Perucca, E. Eur. J. Drug Metab. Pharmacokinet. 20, 15-25 (1995).
8. Marzo, A. Arzneim.-Forsch./Drug Res. 44, 791-793 (1994).
9. Stinson, S.C. C & EN September 21, 83-104 (1998).
10. Jacques, J., Collet, A., and Wilen, S.H. Enantiomers, Racemates and Resolutions. Wiley-Inter-science: New York 1981.
11. Chem. Eng. November 8, 247 (1965).
12. Davis, C.J., Chem. Eng. May 22, 62 (1978).
13. Crosby, J. In: Collins, A.N., Sheldrake, G.N., and Crosby, J. (eds) Chirality in Industry: The Com-mercial Manufacture and Applications of Optically Active Compounds. JohnWiley & Sons: Chi-chester, 1992, pp. 1-66.
14. Wakamatsu, H. Food Eng. November, 92 (1968).
15. Kanoh, S., Hongoh, Y., Motoi, M., and Suda, H. Bull. Chem. Soc. Jpn. 61, 1032-1034 (1988).
16. Doyle, T.R., and Vogl, O. J. Am. Chem. Soc. 111, 8510-8511 (1989).
17. Bellucci., G., Berti, G., Ferretti, M., Mastrorilli, E., and Silvestri, L. J. Org. Chem. 50, 1471-1474 (1985).
18. Jacques, J., and Fouquey, C. Org. Syn. 67, 1-12 (1989).
19. Webster, F.X., Zeng, X.-N., and Silverstein, R.M. J. Org. Chem. 47, 5225-5226 (1982).
20. Paquette, L.A., and Gardlik, J.M. J. Am. Chem. Soc. 102, 5016-5025 (1980).
21. Fizet, C. Helv. Chim. Acta 69, 404-409 (1986).
22. Himmele, W., and Siegel, H. Tetrahedron Lett. 907, 911-914 (1976).
23. Markowicz, S.W. Pol. J. Chem. 53, 157-161 (1979).
24. Faustini, F., DeMunari, S., Panzeri, A., Villa, V, and Gandolfi, C.A. Tetrahedron Lett. 22, 4533-4536 (1981).
25. Perry, C.W., Brossi, A., Deitcher, K.H., Tautz, W., and Teitel, S. Synthesis, 492-494 (1977).
26. Saigo, K., Kai, M., Yonezawa, N., and Hasegawa, M. Synthesis, 214-216 (1985).
27. Corey, E.J., Trybulski, E.J., Melvin Jr, L.S., Nicolaou, K.C., Secrist, J.A., Lett, R., Sheldrake, P.W., Falk, J.R., Brunelle, D.J., Haslanger, M.F., Kim, S., and Yoo, S.-E. J. Am. Chem. Soc. 100, 4618-4620 (1978).
28. Marx, M., Marti, F., Reisdorff, J., Sandmeier, R., and Clark, S. J. Am. Chem. Soc. 99, 6754-6756 (1977).
29. ten Hoeve, W., and Wynberg, H. J. Org. Chem. 50, 4508-4514 (1985).
30. Shiraiwa, T., Sado, Y., Fujii, S., Nakamura, M., and Kurokawa, H. Bull. Chem. Soc. Jpn. 60, 824-826 (1987).
31. Larson, E.R., and Raphael, R.A. J. Chem. Soc. Perkin 1, 521-525 (1982).
32. Suda, H., Motoi, M., Fujii, M., Kanoh, S., and Yoshida, H. Tetrahedron Lett. 4565-4568 (1979).
33. Radier, S., Wermeille, M., and Blaschke, G. Arzneim. Forsch./Drug Res. 45, 1086-1092 (1995).
34. Blaschke, G., and Walther, B. Liebigs Ann. Chem. 561-563 (1987).
35. Abu Zarga, M., and Shamma, M. Tetrahedron Lett., 21, 3739-3742 (1980).
36. Ohgi, T., Kondo, T., and Goto, T. J. Am. Chem. Soc. 101, 3629-3633 (1979).
37. Corey, E.J., Bakshi, R.K., Shibata, S., Chen, C.-P., and Singh, V.K. J. Am. Chem. Soc. 109, 7925-7926 (1987).
38. Hecker, S.J., and Heathcock, C.H., J. Am: Chem. Soc. 108, 4586-4594 (1986).
39. Bey, P., Vevert, J.-P., Van Dorsselaer, V., and Kolb, M. J. Org. Chem. 44, 2732-2742 (1979).
40. Blaschke, G., and Doebler, P. Process for Resolution of Verapamil into its Enantiomers, Ger. Offen DE 3 723 684 (1989).
41. Smith, H.E., Neergaard, J.R., de Paulis, T., and Chen F.-M. J. Am. Chem. Soc. 105, 1578-1584 (1983).
42. Kelly, R.C., Schleuer, I., Stein, S.J., and Wierenga, W. J. Am. Chem. Soc. 101, 1054-1056 (1979).
43. Brown, E., Viot, F., Le Floc'h, Y. Tetrahedron Lett. 26, 4451-4452 (1985).
44. Jacob, III P. J. Org. Chem. 47, 4165-4167 (1982).
45. Smith, H., Burrows, E.P., Marks, M.J., Lynch, R.D., and Chen, F.-M. J. Am. Chem. Soc. 99, 707-713 (1977).
46. Nohira, H., and Ueda, K. Eur Patent Appl EP 65867 (1983), Chem Abstr. 98, 161164v.
47. Viret, J., Patzelt, H., and Collet, A. Tetrahedron Leu. 27, 5865-5868 (1986).
48. Vriesema, B.K., ten Hoeve, W., Wynberg, H., Kellogg, R.M., Boesten, W.H.J., Meijer, E. M., and Schoemaker, H.E. Tetrahedron Lett. 27, 2045-2048 (1986).
49. Cope, A.C., Ganellin, C.R., and Johnson Jr, H.W. J. Am. Chem. Soc. 84, 3191-3192 (1962).
50. Hulshof, L.A., McKervey, M.A., and Wynberg, H. J. Am. Chem. Soc. 96, 3906-3912 (1974).
51. Block Jr, P., and Newman, M.S. Org. Synth. 48, 120-126 (1968).
52. Newman, M.S., and Lutz, W.B. J. Am. Chem. Soc. 78, 2469-2473 (1956).
53. Cramer, F., and Dietsche, W. Chem. Ber. 92, 378-384 (1959).
54. Benschop, H.P., and Van den Berg, G.R. J. Chem. Soc. D, 1431-1432 (1970).
55. Jin, H.L., Stalcup, A., and Armstrong, D.W. Chirality 1, 137-141 (1989).
56. Peacock, S.S., Walba, D.M., Gaeta, F.C.A., Helgeson, R.C., and Cram, D.J. J. Am. Chem. Soc. 102, 2043-2052 (1980).
57. Stoddart, J.F. Top. Stereochem. 17, 207-288 (1987).
58. Yanagihara, R., Tominaga, M., and Aoyama, A. J. Org. Chem. 59, 6865-6867 (1994).
59. Gerdil, R., and Allemand, J. Helv. Chim. Acta 63, 1750-1753 (1980).
60. Gerdil, R. Top. Curr. Chem., 140, 71-105 (1987).
61. Toda, F., Tanaka, K., and Ueda, H. Tetrahedron Lett. 22, 4669-4672 (1981).
62. Toda, F. Top. Curr. Chem. 140, 43-69.(1987).
63. Toda, F., Tanaka, K., and Mak, T.C.W. Chem. Lett. 2085-2088 (1984).
64. Wilen, S.H., Bunding, K.A., Kascheres, C.M., and Wieder, M.J. J. Am. Chem. Soc. 107, 6997-6998 (1985).
65. Pasteur, L. C. R. Acad. Sci. 46, 615 (1858).
66. Johnson, C.R. Acc. Chem. Res. 31, 333-341 (1998).
67. Wang, Y.-F., and Wong, C.-H. J. Org. Chem. 53, 3127-3129 (1988).
68. Coffen, D.L. In: Ahuja, S. (ed.) Chiral Separations, Applications and Technology. ACS: Washington, DC, USA, 1997, Chapter 4, pp. 69-91.
69. Ahuja, S. Chiral Separations, Applications and Technology ACS: Washington, DC, USA, 1997.
70. van Eikeren, P. In: Ahuja, S. (ed.) Chiral Separations, Applications and Technology. ACS: Washington, DC, 1997, pp. 9-35.
71. Wu, S.-H., Guo, Z.-W., and Sih, G.-J. J. Am. Chem. Soc. 112, 1990-1995 (1990).
72. Blanco, L., Guibe-Jampel, E., and Rousseau, G. Tetrahedron. Lett. 29, 1915-1918 (1988).
73. Mutsaers, J.H.G.M., and Kooreman, H.J. Reel. Trav. Chim. Pays-Bas 110, 185-188 (1991).
74. Yamamoto, K., Ueno, Y., Otsubo, K., Kawakami, K., and Komatsu, K. Appl. Environ. Microbiol. 56, 3125-3129 (1990).
75. Hamaguchi, S., Ohashi, T., and Watanabe, K. Agric. Biol. Chem. 50, 375-380 (1986).
76. Chen, C.S., Liu, Y., and Marsella, M.J. Chem. Soc. Perkin Trans. 1, 2559-2562 (1990).
77. Ader, U., and Schneider, M.P. Tetrahedron Asymm. 3, 201-204 (1992).
78. Bertola, M.A., Koger, H.S., Phillips, G.T., Marx, A.F., and Clussen, V.P. European Patent Appl 244, 912 (1987).
79. Habets-Crützen, A.Q.H., Carlier, S.J.N., De Bont, Jan A.M., Wistuba, D., Schurig, V., Hartmans, S., and Tramper, J. Enz. Microb. Technol. 7, 17-21 (1985).
80. Robinson, B.W., Bertola, M.A., Koger, H.S., Mary, A.F., and Watt, P.D. European Patent Appl. 193, 228 (1986).
81. Sheldon, R.A. Chirotechnology (Industrial Synthesis of Optically Active Compounds). Marcel Dekker, Inc.: New York 1993, Chapter 9, pp. 343-385.
82. Bianchi, D., Gabri, W., Cesti, P., Francalanci, F., and Rice, M. J. Org. Chem. 53, 104-107 (1988).
83. Matsuo, N., and Ohno, N. Tetrahedron Lett. 26, 5533-5534 (1985).
84. Finn, M.G., and Sharpless, K.B. In: Morrison, J.D. (ed.) Asymmetric Synthesis. Academic Press, Inc.: Orlando 1985, Vol. 5, pp. 207-308.
85. Hansen, R.M., and Sharpless, K.B. J. Org. Chem. 51, 1922-1925 (1996).
86. Sharpless, K.B. Janssen Chim. Acta 6, 3-9 (1988).
87. Gao, Y., Hanson, R.M., Klunder, J.M., Ko, S.Y., Massamane, H., and Sharpless, K.B. J. Am. Chem. Soc. 109, 5765-5780 (1987).
88. Kitamura, M., Kasahara, I., Manabe, K., and Noyori, R. J. Org. Chem. 53, 708-710 (1988).
89. Gil-Av, E, Feibush, B., and Charles-Sigler, R. Tetrahedron Lett. 10, 1009-1015 (1966).
90. Schurig, V. J. Chromatogr. A 666, 111-129 (1994).
91. König, W.A. Gas Chromatographic Enantiomer Separation with Modified Cyclodextrins John Wiley & Sons: Chichester, England, 1989.
92. König, W.A. In: Wainer, I.W., and Drayer, D.E. (eds) Drug Stereochemistry (Analytical Methods and Pharmacology). Marcel Dekker, Inc.: New York, 1988, Chapter 5, pp. 113-145.
93. Beesley, T.E., and Scott, R.P.W. Chiral Chromatography. John Wiley & Sons: Chichester, 1998, Chapter 6, pp. 141-172.
94. Hall, A.C., Lieb, W.R., and Franks, N.P. Br. J. Pharmacol. 112, 906-910 (1994).
95. Garton, K.J., Yuen, P., Meinwald, J., Thummel, E.D., Kharasch, D., and Evan, D. Drug Metab. Disp. 23, 1426-1430 (1995).
96. Meinwald, J., Thompson, W.R., Pearson, D.L., König, W.A., Runge, T., and Francke, W. Science, 251, 560-561 (1991).
97. Schurig, V., Grosenick, H., and Green, B.S. Angew. Chem. Int. Ed. Engl. 32, 1690-1691 (1993).
98. Shitangkoon, A., Staerk, D.U., and Vigh, G. J. Chromatogr. A 657, 387-394 (1993).
99. Staerk, D.U., Shitangkoon, A., and Vigh, G. J. Chromatogr. A 677, 133-140 (1994).
100. Juza, M., Di Giovanni, O., Biressi, G., Schurig, V., Mazzoti, M., and Morbidelli, M. J. Chromatogr. A, 813, 333-347 (1998).
101. Storti, G., Mazzoti, M., Furlan, L.T., Morbidelli, S., and Carra, S. Sep. Sci. Technol. 27, 1889-1916 (1992).
102. Mazzoti, M., Baciocchi, R., Storti, G., and Morbidelli, M. Ind. Eng. Chem. Res. 35, 2313-2321 (1996).
103. Lemko, C.H., Gilles, C., and Foster, R.T. J. Chromatogr. 619, 330-335 (1993).
104. Lindner, W. In: Zief, M., and Crane, L.J. (eds) Chromatographic Chiral Separations. (Chromatographic Science Series, 40), Dekker Inc.: New York, 1988, Chapter 4, pp. 91-130.
105. Davankov, V.A. Chromatographia 27, 475-482 (1989).
106. LePage, J., Lindner, W., Davies, G., and Karger, B. Anal. Chem. 51, 433-435 (1979).
107. Hare, P.E., and Gil-Av, E. Science, 204, 1226-1228 (1979).
108. Sybilska, D., and Zukowski, J. In: Krstulovic, A.M. (ed.) Chiral Separations by HPLC. Ellis Hor-wood Limited: New York, 1989, Chapter 7, pp. 124-172.
109. Nimura, N. In: Krstulovic, A.M. (ed.) Chiral Separations by HPLC. Ellis Horwood Limited: New York, 1989, Chapter 5, pp. 107-123.
110. Petersson, C., and Heldin, E. In: Subramanian, G. (ed.) A Practical Approach to Chiral Separations by Liquid Chromatography. VCH: Weinheim, Germany, 1994, Chapter 9, pp. 279-310.
111. Cooper, A.D., and Jefferies, T.M. J. Chromatogr. 637, 137-143 (1993).
112. Davankov, V.A. In: Krstulovic, A.M. (ed.) Chiral Separations by HPLC. Ellis Horwood Limited: New York, 1989, Chapter 8, pp. 175-193.
113. Welch, C.J. J. Chromatogr. A 666, 3-26 (1994).
114. Alienmark, S.G., and Andersson, S. J. Chromatogr. A 666, 167-179 (1994).
115. Okamoto, Y., and Yashima, E. Angew. Chem. Int. Ed. 37, 1073-1095 (1998).
116. Stalcup, A. In: Subramanian, G. (ed.) A Practical Approach to Chiral Separations by Liquid Chromatography. VCH: Weinheim, Germany, 1994, Chapter 5, pp. 95-113.
117. Okamoto, Y., and Hatada, K. In: Zief, M., and Crane, L.J. (eds) Chromatographic Chiral Separations. (Chromatographic Science Series, 40), Marcel Dekker Inc: New York, 1988, Chapter 8, pp.199-218.
118. Sellergren, B. In: Krstulovic, A.M. (ed.) Chiral Separations by HPLC. Ellis Horwood Limited: New York, 1989, Chapter 4, pp. 69-92.
119. Kinkel, J.N. In: Krstulovic, A.M. (ed.) Chiral Separations by HPLC. Ellis Horwood Limited: New York, 1989, Chapter 8, pp. 217-269.
120. Krause, K., Girod, M., Chankvetadze, B., and Blaschke, G. J. Chromatog. A, in press (1999).
121. Noctor, T.A.G. In: Subramanian, G. (ed.) A Practical Approach to Chiral Separations by Liquid Chromatography. VCH: Weinheim, 1994, Chapter 12, pp. 357-396.
122. Henderson, G.M., and Rule, H.G. J. Chem. Soc. 1568-1573 (1939).
123. Lecoq, H. Bull. Soc. Ray Sci. Liege 11, 318-325 (1943).
124. Prelog, V., and Wieland, P. Helv. Chim. Acta 27, 1127-1134 (1944).
125. Mayer, W., and Merger, F. Liebigs Ann. Chem. 644, 65-69 (1961).
126. Lautsch, W., and Heinicke, D. Kolloid Z. 154, 1-4 (1957).
127. Blaschke, G., and Markgraf, H. Chem. Ber. 113, 2031-2035 (1980).
128. Blaschke, G., and Maibaum, J. J. Pharm. Sci. 74, 438-442 (1985).
129. Blaschke, G., Fraenkel, B., Fröhlingsdorf, B., and Marx, A. Liebigs Ann. Chem. 8, 753-756 (1988).
130. Allenmark, S., and Thompson, R.A. Tetrahedron Lett. 28, 3751-3752 (1987).
131. Rimböck, K.H., Kastner, F., and Mannschreck, A. J. Chromatogr. 329, 307-310 (1985).
132. Francotte, E., Stierlin, H., and Faigle, J.W. J. Chromatogr. 346, 321-331 (1985).
133. Furet, P., Batze, C., Bhatnagor, A., Francotte, E., Rihs, G., and Lang, M. J. Med. Chem. 36, 1393-1400 (1993).
134. Willstätter, R. Ber. Dtsch. Chem. Ges. 37, 3758-3760 (1904).
135. Blaschke, G., and Donow, F. Chem. Ber. 108, 1188-1197 (1975).
136. Blaschke, G. Angew. Chem. 92, 14-25 (1980).
137. Blaschke, G., Kraft, H.P., Fikentscher, K., and Köhler, F. Arzneim. Forsch. 29, 1640-1642 (1979).
138. Francotte, E., and Junker-Buchheit, A. J. Chromatogr. 576, 1-45 (1992).
139. Francotte, E. J. Chromatogr. A 666, 565-601 (1994).
140. Francotte, E. In: Ahuja, S. (ed.) Chiral Separations (Applications and Technology). ACS: Washington, DC, USA, 1997, Chapter 10, pp. 271-308.
141. Rimböck, K.H., Kastner, F., and Mannschreck, A. J. Chromatogr. 351, 346-350 (1986).
142. Francotte, E., and Wolf, R.M. Chirality 3, 43-55 (1991).
143. Vigh, G., Quintero, G., and Farkas, G. J. Chromatogr. 484, 237-250 (1989).
144. Farkas, G., Irgens, L.H., Quintero, G., Beeson, M.D., Al-Saed, A., and Vigh, G. J. Chromatogr. 645, 67-74 (1993).
145. Irgens, L.H., Farkas, G., and Vigh, G. J. Chromatogr. A 666, 603-609 (1994).
146. Martin, A.J.P. In: Coates, Y.J., Noebles, H.J., and Fagerson, I.S. (eds) Gas Chromatography. Academic Press: New York, 1958, p. 237.
147. Biesenberger, J.A., Tan, M., Duvdevan, I., and Maurer, T. J. Polym. Sci. 9, 353-357 (1971).
148. Dingenen, J., and Kinkel, J.N. J. Chromatogr. A 666, 627-650 (1994).
149. Chizhkov, V.P. (Russ. Chem. Rev.), Usp. Khim. 40, 161-175 (1971).
150. Martin, M., Vorillon, F., Eon, C., and Guiochon, G. J. Chromatogr. 125, 17-41 (1976).
151. Saidel-Morgenstern, A., and Guiochon, G. Chem. Eng. Sci. 48, 2787-2797 (1993).
152. Dingenen, J. In: Subramanian, G. (ed.) A Practical Approach to Chiral Separations by Liquid Chromatography. VCH: Weinheim, New York, 1994, Chapter 6, pp. 115-181.
153. Devant, M.R., Jonas, R., Schulte, M., Keil, A., and Charten, F. J. Prakt. Chem. 339, 315-321 (1997).
154. Schulte, M., Ditz, R., Devant, R.M., Kinkel, J.N., and Charton, F. J. Chromatogr. A 769, 93-100 (1997).
155. Schulte, M., 10th International Symposium on Chiral Discrimination, Vienna, Austria (1998).
156. Jonas, R., Klockow, M., Lues, I., and Wurziger, H. Bioorg. Med. Chem. Lett. 4, 2585-2588 (1994).
157. Negawa, M., and Shoji, F. J. Chromatogr. 590, 113-117 (1992).
158. Fuchs, G., Nicoud, R.M., and Bailly, M. Proceedings of the 9th Symposium on Preparative and Industrial Chromatography, "Prep 92" INPL, Nancy, France, 1992, pp. 205-220.
159. Nicoud, R.M., Fuchs, G., Adam, P., Bailly, M., Küsters, E., Antia, F.D., Reuill, R., and Schmid, E. Chirality 5, 267-271 (1993).
160. Nicoud, R.M., Bailly, M., Kinkel, R., Devant, R., Hampe, T., and Küsters, E. In: Nicoud, R.M. (ed.) Simulated Moving Bed: Basics and Applications. INPL, Nancy, France, 1993, pp. 65-88.
161. Ching, C.B., Lim, B.G., Lee, E.J.D., and Ng, S.C. J. Chromatogr. 634, 215-219 (1993).
162. Guest, D.W. J. Chromatogr. A 760, 159-162 (1997).
163. Cavoy, E., Deltent, M.F., Lehoucq, S., and Miggiano, D. J. Chromatogr. A 769, 49-57 (1997)
164. Blehaut, J. 10th International Symposium on Chiral Discrimination, Vienna, Austria (1998)
165. Gattuso, M.J., and Makino, S. Poster Presentation on Chiral 94, Reston, VA, (1994).
166. Francotte, E.R., and Richert, P. J. Chromatogr. 769, 101-107 (1997).
167. Seebach, D., Hoffmann, M., Sting, A.R., Kinkel, J.N., Schulte, M., and Küsters, E. J. Chromatogr. A 796, 299-307 (1998).
168. Macaudiere, P., Caude, M., Rosset, R., and Tambute, A. J. Chromatogr. Sci. 27, 383-394 (1989).
169. Fuchs, G., Doguet, L., Perrut, M., Tambute, A., and Le Goff, P. Presentation at the Symposium on Supercritical Fluids, Boston, MA, USA (1991).
170. Blum, A.M., and Kumar, M.L. Poster Presentation at the 4th International Symposium on Chiral Discrimination, Montreal, Canada, September (1993).
171. Fuchs, G., Doguet, L., Barth, D., and Perrut, M. J. Chromatogr. 623, 329-336 (1992).
172. Stalcup, A.M., Gahm, K.H., Gratz, S.R., and Sutton, R.M.C. Anal. Chem. 70, 144-148 (1998).
173. Chankvetadze, B. Capillary Electrophoresis in Chiral Analysis John Wiley & Sons: Chichester, England, 1997.
174. Krause, K., Chankvetadze, B., Okamoto, Y., and Blaschke, G. Electrophoresis, 20, 2772-2778 (1999).
175. Reider, P.J., Davis, P., Hughes, L.D., and Grabowski, E.J.S. J. Org. Chem. 52, 955-957 (1987).
176. Black, S.N., Williams, L.J., Davey, R.J., Moffatt, F., Jones, R.V.H., McEwan, D.M., and Sadler, D.E. Tetrahedron 45, 2677-2682 (1989).
177. Sifiniades, S., Boyle, W.J.J., and Van Peppen, J.F. J. Am. Chem. Soc. 98, 3738-3739 (1976).
178. Kamphuis, J., Boesten, W.H., Kaptein, B., Hermes, H.F.M., Sanke, T., Broxterman, Q.B., Van den Tweel, W.J.J., and Schoemaker, H.E. In: Collins, A.N., Sheldrake, G.N., and Crosby, J. (eds) Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds. John Wiley & Sons: Chichester, 1992, Chapter 8, pp. 187-208.
179. Belokon, Y.N., Tararov, V.I., Saveleva, T.F., and Belikov, V.M., Makrom. Chem. 187, 1077-1086 (1986).
180. Chibata, I., Yamada, S., Hongo, C., and Yochioka, R. European Patent Appl., 0. 070. 114 (1982).
181. Kral, V., Dvorak, D., Javada, J., Stibor, I., Mostecky, J., and Votava, V. Czechoslovakian Patent, 257094 (1989), CA: 112, 35450 (1990).
182. Kamphuis, J., Boesten, W.H.J., Broxterman, Q.B., Hermes, H.F.M., van Balken, J.A.M., Meijer, E.M., and Schoemaker, H.E. Adv. Biochem. Eng./Biotechnol. 42, 133-186 (1990).
183. Guivarch, M., Gillonier, C., and Brunie, J.C.. Bull. Soc. Chem. Fr. 44, 91-95 (1980)
184. Nishida, Y., Nakamichi, K., Nabe, K., and Tosa, T. Enzyme Microb. Technol. 9, 479-483 (1987).
185. Syldatk, C., and Wagner, F. Food Biotechnol. 4, 87-95 (1990).