Polysaccharide derivatives for chromatographic separation of enantiomers

Angewandte Chemie - International Edition

Volumn 37, Issue 8, 1998, Pages 1020-1043

  Okamoto, Yoshio ^a   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Chirality; Enantiomeric resolution; Liquid chromatography; Molecular recognition; Polysaccharides

Indexed keywords

EID: 0032482102     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980504)37:8<1020::aid-anie1020>3.0.co;2-5     Document Type: Review

References (309)

1. G. Blaschke, Angew. Chem. 1980, 92, 14-25; Angew. Chem. Int. Ed. Engl. 1980, 19, 13-24.
2. G. Blaschke, Angew. Chem. 1980, 92, 14-25; Angew. Chem. Int. Ed. Engl. 1980, 19, 13-24.
3. G. Blaschke, H. P. Kraft, K. Fickentscher, F. Kohler, Arzneim. Forsch. 1979, 29, 1640-1642.
4. a) G. W. Muller, CHEMTECH 1997, 27(1), 21-25;
5. b) S. C. Stinson, Chem. Eng. News 1994, 72 (September 19), 38-72.
6. a) Chiral Separations-Applications and Technology (Ed.: S. Ahuja), American Chemical Society, Washington, DC, 1997;
7. b) S. G. Allenmark, Chromatographic Enantioseparation, Ellis Horwood, Chichester, 1988;
8. c) A Practical Approach to Chiral Separations by Liquid Chromatography (Ed.: G. Subramanian), VCH, New York, 1994;
9. d) D. W. Armstrong, Anal. Chem. 1987, 59, 84A-91A;
10. e) Y. Okamoto, CHEMTECH 1987, 176-181;
11. f) W. H. Pirkle, T. C. Pochapsky, Chem. Rev. 1989, 89, 347-362;
12. g) D. R. Taylor, K. Maher, J. Chromatogr. Sci. 1992, 30, 67-85.
13. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 214-274.
14. E. Yashima, C. Yamamoto, Y. Okamoto, Synlett 1998, in press.
15. a) I. M. Mutton in A Practical Approach to Chiral Separations by Liquid Chromatography (Ed.: G. Subramanian), VCH, New York, 1994, chap. 11, pp. 329-355;
16. b) The Impact of Stereochemistry on Drug Development and Use (Eds.: H. Y. Aboul-Enein, I. W. Wainer), Wiley, New York, 1997.
17. a) B. Waldeck, Chirality 1993, 5, 350-355;
18. b) J. S. Millership, A. Fitzpatrick, ibid. 1993, 5, 573-576;
19. c) J. Caldwell, J. Chromatogr. A 1995, 694, 39-48;
20. d) G. Pifferi, E. Perucca, Eur. J. Drug Metab. Pharmacokinet. 1995, 20, 15-25.
21. a) A. G. Rauws, K. Groen, Chirality 1994, 6, 72-75;
22. b) J. Caldwell, J. Chromatogr. A 1996, 719, 3-13;
23. c) S. Ahuja in The Impact of Stereochemistry on Drug Development and Use (Eds.: H. Y. Aboul-Enein, I. W. Wainer), Wiley, New York, 1997, chap. 10, pp. 287-315.
24. a) S. C. Stinson, Chem. Eng. News 1992, 70 (September 28), 46-79;
25. b) S. C. Stinson, ibid. 1995, 73 (October 9), 44-78.
26. a) S. C. Chang, G. L. Reid III, C. D. Chang, D. W. Armstrong, Trends Anal. Chem. 1993, 12, 144-153;
27. b) C. J. Welch, Adv. Chromatogr. 1995, 35, 171-197;
28. c) W. H. Pirkle, L. J. Brice, G. J. Terfloth, J. Chromalogr. A 1996, 753, 109-119.
29. W. H. Pirkle, J. M. Finn, J. L. Schreiner, B. C. Hamper, J. Am. Chem. Soc. 1981, 103, 3964-3966.
30. G. Blaschke, J. Liq. Chromatogr. 1986, 9, 341-368.
31. a) Y. Okamoto, I. Okamoto, H. Yuki, S. Murata, R. Noyori, H. Takaya, J. Am. Chem. Soc. 1981, 103, 6971-6973;
32. b) Y. Okamoto, K. Hatada, J. Liq. Chromatogr. 1986, 9, 369-384;
33. c) T. Nakano, Y. Okamoto, K. Hatada, J. Am. Chem. Soc. 1992, 114, 1318-1329;
34. d) Y. Okamoto, T. Nakano, Chem. Rev. 1994, 94, 349-372;
35. e) T. Nakano, Y. Okamoto, K. Hatada, Polym. J. 1995, 27, 882-891.
36. a) T. Shibata, I. Okamoto, K. Ishii, J. Liq. Chromatogr. 1986, 9, 313-340;
37. b) Y. Okamoto, R. Aburatani, K. Hatano, K. Hatada, ibid. 1988, 11, 2147-2163;
38. c) A. Ichida, T. Shibata in Chromatographic Chiral Separations (Eds.: M. Zief, L. J. Crane), Marcel Dekker, New York, 1990, chap. 9, pp. 219-243;
39. d) Y. Okamoto, Y. Kaida, J. Chromatogr. A 1994, 666, 403-419;
40. e) J. Dingene in A Practical Approach to Chiral Separations by Liquid Chromatography (Ed.: G. Subramanian), VCH, New York, 1994, chap. 6, pp. 115-181;
41. f) K. Oguni, H. Oda, A. Ichida, J. Chromatogr. A 1995, 694, 91-100;
42. g) E. Yashima, Y. Okamoto, Bull. Chem. Soc. Jpn. 1995, 68, 3289-3307;
43. h) E. Yashima, Y. Okamoto in The Impact of Stereochemistry on Drug Development and Use (Eds.: H. Y. Aboul-Enein, I. W. Wainer), Wiley, New York, 1997, chap. 12, pp. 345-376.
44. a) G. Wulff, Angew. Chem. 1995, 107, 1958-1979; Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832;
45. a) G. Wulff, Angew. Chem. 1995, 107, 1958-1979; Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832;
46. b) D. Kriz, O. Ramström, K. Mosbach, Anal. Chem. 1997, 69, 345A-349A.
47. a) E. Francotte, J. Chromatogr. A 1992, 576, 1-45;
48. b) E. Francotte, ibid. 1994, 666, 565-601;
49. c) E. Francotte in The Impact of Stereo-chemistry on Drug Development and Use (Eds.: H. Y. Aboul-Enein, I. W. Wainer), Wiley, New York, 1997, chap. 23, pp. 633-683;
50. d) E. Francotte in Chiral Separations (Applications and Technology (Ed.: S. Ahuja), American Chemical Society, Washington, DC, 1997, chap. 10, pp. 271-308.
51. a) A. W. Ingersoll, R. Adams, J. Am. Chem. Soc. 1922, 44, 2930-2937;
52. b) C. W. Porter, H. K. Ihrig, ibid. 1923, 45, 1990-1993.
53. G. M. Henderson, H. G. Rule, Nature 1938, 141, 917-918.
54. V. Prelog, P. Wieland, Helv. Chim. Acta 1944, 27, 1127-1134.
55. M. Kotake, T. Sakan, N. Nakamura, S. Senoh, J. Am. Chem. Soc. 1951, 73, 2973-2974.
56. a) C. Dalgliesh, J. Chem. Soc. 1952, 3940-3942;
57. b) L. H. Basson, E. Stedman, Biochem. J. 1933, 27, 1257-1266.
58. S. F. Contractor, J. Wragg, Nature 1965, 208, 71-72.
59. a) H. Krebs, J. A. Wagner, J. Diewald, Chem. Ber. 1956, 89, 1875-1883;
60. b) L. T. Taylor, D. H. Busch, J. Am. Chem. Soc. 1967, 89, 5372 -5376;
61. c) G. Konrad, H. Musso, Liebigs Ann. Chem. 1986, 1956-1967.
62. H. Hess, G. Burger, H. Musso, Angew. Chem. 1978, 90, 645-646; Angew. Chem. Int. Ed. Engl. 1978, 17, 612-614.
63. H. Hess, G. Burger, H. Musso, Angew. Chem. 1978, 90, 645-646; Angew. Chem. Int. Ed. Engl. 1978, 17, 612-614.
64. a) S. Yuasa, M. Itoh, S. Shimada, J. Chromatogr. Sci. 1984, 22, 288-292;
65. b) T. Fukuhara, M. Isoyama, A. Shimada, M. Itoh, S. Yuasa, J. Chromatogr. 1987, 387, 562-565.
66. a) G. R. Brubaker, J. I. Legg, J. Am. Chem. Soc. 1966, 88, 3446;
67. b) Y. Yoshikawa, K. Yamasaki, Coord. Chem. Rev. 1979, 25, 205-229;
68. c) H. Yoneda, J. Chromatogr. 1985, 313, 59-91.
69. G. Wulff, S. Kubik, H.-G. Breitinger in Nachwachsende Rohstoffe-Perspektiven für die Chemie (Eds.: M. Eggersdorfer, S. Warwel, G. Wulff), VCH, Weinheim, 1993, pp. 311-322.
70. a) T. J. Ward, Anal. Chem. 1994, 66, 633A-640A.
71. b) A. M. Stalcup, N. M. Agyei, ibid. 1994, 66, 3054-3059;
72. c) B. Chankvetadze, M. Saito, E. Yashima, Y. Okamoto, J. Chromatogr. A 1997, 773, 331-338.
73. a) M. Novotny, H. Soini, M. Stefansson, Anal. Chem. 1994, 66, 646A-655A;
74. b) S. Terabe, K. Ohtsuka, H. Nishi, J. Chromatogr. A 1994, 666, 295-319;
75. c) H. Nishi, S. Terabe, J. Chromatogr. Sci. 1995, 33, 698-703;
76. d) H. Nishi, J. Chromatogr. A 1996, 735, 57-76.
77. P. Salvadori, C. Bertucci, C. Rosini in Circular Dichroism-Principles and Applications (Eds.: K. Nakanishi, N. Berova, R. W. Woody), VCH, New York, 1994, chap. 20, pp. 541-560.
78. a) G. Hesse, R. Hagel, Chromatographia 1973, 6, 277-280;
79. b) G. Hesse, R. Hagel, Liebigs Ann. Chem. 1976, 966-1008.
80. a) A. Lüttringhaus, U. Hess, H. J. Rosenbaum, Z. Naturforsch. B 1967, 22, 1296-1300;
81. b) A. Lüttringhaus, K. C. Peters, Angew. Chem. 1966, 78, 603; Angew. Chem. Int. Ed. Engl. 1966, 5, 593.
82. b) A. Lüttringhaus, K. C. Peters, Angew. Chem. 1966, 78, 603; Angew. Chem. Int. Ed. Engl. 1966, 5, 593.
83. a) I. Pettersson, U. Berg, J. Chem. Res. Synop. 1984, 208-209;
84. b) K. Schlögl, M. Widhalm, Chem. Ber. 1982, 115, 3042-3048;
85. c) R. Isaksson, J. Rochester, J. Sandström, L.-G. Wistrand, J. Am. Chem. Soc. 1985, 107, 4074-4075;
86. d) M. P. Schneider, H. Bippi, ibid. 1980, 102, 7363-7365;
87. e) W. Boland, U. Niedermeyer, L. Jaenicke, H. Görisch, Helv. Chim. Acta 1985, 68, 2062-2073;
88. f) H. Koller, K.-H. Rimböck, A. Mannschreck, J. Chromatogr. 1983, 282, 89-94;
89. g) K. Schlögl, A. Werner, M. Widhalm, J. Chem. Soc. Perkin Trans. 1 1983, 1731-1735;
90. h) I. Agranat, M. R. Suissa, S. Cohen, R. Isaksson, J. Sandström, J. Dale, D. Grace, J. Chem. Soc. Chem. Commun. 1987, 381-383;
91. i) G. Lindsten, O. Wennerström, R. Isaksson, J. Org. Chem. 1987, 52, 547-554.
92. a) Y. Okamoto, M. Kawashima, K. Yamamoto, K. Hatada, Chem. Lett. 1984, 739-742;
93. b) A. Ichida, T. Shibata, I. Okamoto, Y. Yuki, H. Namikoshi, Y. Toda, Chromatographia 1984, 19, 280-284.
94. Y. Okamoto, R. Aburatani, K. Hatada, J. Chromatogr. 1987, 389, 95-102.
95. a) E. J. Corey, M. A. Letavic, J. Am. Chem. Soc. 1995, 117, 9616-9617;
96. b) M. Amadji, J. Vadecard, J.-C. Plaquevent, L. Duhamel, P. Duhaniel, ibid. 1996, 118, 12483-12484;
97. c) K. Kimata, M. Kobayashi, K. Hosoya, T. Araki, N. Tanaka, ibid. 1996, 118, 759-762;
98. d) M. Cavazza, M. Zandomeneghi, A. Ouchi, Y. Koga, ibid. 1996, 118, 9990-9991;
99. e) M. Nakajima, Y. Sasaki, M. Shiro, S. Hashimoto, Tetrahedron: Asymmetry 1997, 8, 341-344;
100. f) H. Hara, S. Komoriya, T. Miyashita, O. Hoshino, ibid. 1995, 6, 1683-1692;
101. g) S. Takeuchi, A. Ohira, N. Miyoshi, H. Mashio, Y. Ohga, ibid. 1994, 5, 1763-1780;
102. h) K. Okada, M. Mikami, M. Oda, Chem. Lett. 1993, 1999-2002.
103. a) W. Adam, P. Groer, C. R. Saha-Möller, Tetrahedron: Asymmetry 1997, 8, 833-836;
104. b) T. Biadatti, J. L. Esker, C. R. Johnson, ibid. 1996, 7, 2313-2320;
105. c) M. W. Miller, C. R. Johnson, J. Org. Chem. 1997, 62, 1582-1583.
106. K.-H. Rimböck, F. Kastner, A. Mannschreck, J. Chromatogr. 1986, 351, 346-350.
107. a) E. Francotte, R. M. Wolf, Chirality 1991, 3, 43-55;
108. b) J. Chromatogr. 1992, 595, 63-75;
109. c) E. Francotte, T. Zhang, J. Chromatogr. A 1995, 718, 257-266.
110. Y. Okamoto, M. Kawashima, K. Hatada, J. Chromatogr. 1986, 363, 173-186.
111. a) B. Chankvetadze, E. Yashima, Y. Okamoto, J. Chromatogr. A 1994 670, 39-49;
112. b) E. Yashima, C. Yamamoto, Y. Okamoto, Polym. J. 1995, 27, 856-861;
113. c) B. Chankvetadze, L. Chankvetadze, S. Sidamonidze, E. Kasashima, E. Yashima, Y. Okamoto, J. Chromatogr. A 1997, 787, 67-77.
114. Y. Okamoto, R. Aburatani, T. Fukumoto, K. Hatada, Chem. Lett. 1987, 1857-1860.
115. a) Y. Okamoto, T. Ohashi, Y. Kaida, E. Yashima, Chirality 1993, 5, 616-621;
116. b) B. Chankvetadze, E. Yashima, Y. Okamoto, J. Chromatogr. A 1995, 694, 101-109.
117. a) H. Steinmeier, P. Zugenmaier, Carbohydr. Res. 1987, 164, 97-105;
118. b) U. Vogt, P. Zugenmaier, Ber. Bunsen-Ges. Phys. Chem. 1985, 89, 1217-1224.
119. U. Vogt, P. Zugenmaier, Communication at the European Science Foundation Workshop on Specific Interaction in Polysaccharide Sysmtems, Uppsada, Sweden, 1983.
120. a) Y. Okamoto, R. Aburatani, S. Miura, K. Hatada, J. Liq. Chromatogr. 1987, 10, 1613-1628;
121. b) E. Yashima, H. Fukaya, Y. Okamoto, J. Chromatogr. A 1994, 677, 11-19.
122. Y. Okamoto, M. Kawashima, R. Aburatani, K. Hatada, T. Nishiyama, M. Masuda, Chem. Lett. 1986, 1237-1240.
123. a) K. Tashiro, K. Konishi, T. Aida, Angew. Chem. 1997, 109, 882-884; Angew. Chem. Int. Ed. Engl. 1997, 36, 856-858;
124. a) K. Tashiro, K. Konishi, T. Aida, Angew. Chem. 1997, 109, 882-884; Angew. Chem. Int. Ed. Engl. 1997, 36, 856-858;
125. b) H. Hopf, W. Grahn, D. G. Barrett, A. Geldes, J. Hilmer, J. Hucker, Y. Okamoto, Y. Kaida, Chem. Ber. 1990, 123, 841-844;
126. c) M. Yoshifuji, Y. Ichikawa, K. Toyota, E. Kasashima, Y. Okamoto, Chem. Lett. 1997, 87-88;
127. d) T. Mizutani, T. Ema, T. Tomita, Y. Kuroda, H. Ogoshi, J. Am. Chem. Soc. 1994, 116, 4240-4250;
128. e) A. Ohno, J. Kunitomo, Y. Kawai, T. Kawamoto, M. Tomishima, F. Yoneda, J. Org. Chem. 1996, 61, 9344-9355;
129. f) Y. Ito, T. Ohara, R. Shima, M. Suginome, J. Am. Chem. Soc. 1996, 118, 9188-9189;
130. g) T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, ibid. 1995, 117, 9101-9102;
131. h) S. E. Biali, B. Kahr, Y. Okamoto, R. Aburatani, K. Mislow, ibid. 1988, 110, 1917-1922;
132. i) E. J. Corey, B. E. Roberts, B. R. Dixon, ibid. 1995, 117, 193-196;
133. j) C. J. Helal, P. A. Magriotis, E. J. Corey, ibid. 1996, 118, 10938-10939;
134. k) E. J. Corey, R. S. Kania, ibid. 1996, 118, 1229-1230;
135. l) M. E. Flanagan, J. R. Jacobsen, E. Sweet, P. G. Schultz, ibid. 1996, 118, 6078-6079;
136. m) T. Shibata, H. Morioka, T. Hayase, K. Choji, K. Soai, ibid. 1996, 118, 471-472;
137. n) M. Shimano, A. I. Meyers, ibid. 1994, 116, 6437-6438;
138. o) A. R. Muci, K. R. Campos, D. A. Evans, ibid. 1995, 117, 9075-9076;
139. p) V. Gracias, G. L. Milligan, J. Aubé, ibid. 1995, 117, 8047-8048;
140. q) A. Viso, N. E. Lee, S. L. Buchwald, ibid. 1994, 116, 9373-9374;
141. r) D. L. Boger, J. A. McKie, T. Nishi, T. Ogiku, ibid. 1997, 119, 311-325;
142. s) B. M. Trost, M. J. Krishe, R. Radinov, G. Zanoni, ibid. 1996, 118, 6297-6298;
143. t) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, ibid. 1996, 118, 4916-4917;
144. u) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642;
145. u) C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642;
146. v) H. Rieck, G. Helmchen, ibid. 1995, 107, 2881-2883 and 1995, 34, 2687-2689;
147. v) H. Rieck, G. Helmchen, ibid. 1995, 107, 2881-2883 and 1995, 34, 2687-2689;
148. w) S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, ibid. 1997, 109, 300-303 and 1997, 36, 288-290;
149. w) S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, ibid. 1997, 109, 300-303 and 1997, 36, 288-290;
150. x) S. Itsuno, K. Watanabe, K. Ito, A. A. El-Shehawy, A. A. Sarhan, ibid. 1997, 109, 105-107 and 1997, 36, 109-110;
151. x) S. Itsuno, K. Watanabe, K. Ito, A. A. El-Shehawy, A. A. Sarhan, ibid. 1997, 109, 105-107 and 1997, 36, 109-110;
152. y) O. Brümmer, A. Rückert, S. Blechert, Chem. Eur. J. 1997, 3, 441-446;
153. z) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. 1997, 109, 379-381; Angew. Chem. Int. Ed. Engl. 1997, 36, 410-411.
154. z) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. 1997, 109, 379-381; Angew. Chem. Int. Ed. Engl. 1997, 36, 410-411.
155. a) K. P. M. Vanhessche, K. B. Sharpless, Chem. Eur. J. 1997, 3, 517-522;
156. b) T. Nagata, K. Yorozu, T. Yamada, T. Mukaiyuma, Angew. Chem. 1995, 107, 2309-2311; Angew. Chem. Int. Ed. Engl. 1995, 34, 2145-2147;
157. b) T. Nagata, K. Yorozu, T. Yamada, T. Mukaiyuma, Angew. Chem. 1995, 107, 2309-2311; Angew. Chem. Int. Ed. Engl. 1995, 34, 2145-2147;
158. c) Y. Kondo, T. Matsudaira, J. Sato, N. Murata, T. Sakamoto, ibid. 1996, 108, 818-820 and 1996, 35, 736-738;
159. c) Y. Kondo, T. Matsudaira, J. Sato, N. Murata, T. Sakamoto, ibid. 1996, 108, 818-820 and 1996, 35, 736-738;
160. d) A. Yanagisawa, A. Ishiba, H. Nakashima, H. Yamamoto, Synlett 1997, 88-90;
161. e) A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 4723-4724.
162. Y. Okamoto, R. Aburatani, K. Hatada, J. Chromatogr. 1988, 448, 454-455.
163. S. Habaue, H. Sakamoto, Y. Okamoto, Polym. J. 1997, 29, 384-386.
164. M. Taki, S. Sugita, Y. Nakamura, E. Kasashima, E. Yashima, Y. Okamoto, J. Nishimura, J. Am. Chem. Soc. 1997, 119, 926-932.
165. K. Maeda, Y. Okamoto, N. Morlender, N. Haddad, I. Eventova, S. E. Biali, Z. Rappoport, J. Am. Chem. Soc. 1995, 117, 9686-9689.
166. a) C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548;
167. b) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944.
168. b) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944.
169. a) A. Ikeda, M. Yoshimura, P. Lhotak, S. Shinkai, J. Chem. Soc. Perkin Trans. 1 1996, 1945-1950;
170. b) H. Otsuka, S. Shinkai, Supramol. Chem. 1996, 3, 189-205;
171. c) T. Kawahata, K. Yahiro, K. Fujii, J. Am. Chem. Soc. 1991, 113, 9694-9696;
172. d) S. Toyota, T. Akinaga, H. Kojima, M. Aki, M. Oki, ibid. 1996, 118, 11 460-11 466;
173. e) M. S. Iyer, K. M. Gigstad, N. D. Namdev, M. Lipton, ibid. 1996, 118, 4910-4911;
174. f) B. Orsat, P. B. Alper, W. Moree, C.-P. Mak, C.-H. Wong, ibid. 1996, 118, 712-713;
175. g) B. M. Trost, R. Radinov, ibid. 1997, 119, 5962-5963;
176. h) Y. Hayashi, J. J. Rohde, E. J. Corey, ibid. 1996, 118, 5502-5503;
177. i) B. M. Trost, S. Tanimori, P. T. Dunn, ibid. 1997, 119, 2735-2736;
178. j) E. J. Corey, M. C. Noe, ibid. 1996, 118, 11038-11053;
179. k) D. W. Nelson, A. Gypser, P. T. Ho, H. C. Kolb, T. Kondo, H.-L. Kwong, D. V. McGrath, A. E. Rubin, P.-O. Norrby, K. P. Gable, K. B. Sharpless, K. B. ibid. 1997, 119, 1840-1858;
180. l) H. Becher, K. B. Sharpless, Angew. Chem. 1996, 108, 447-449; Angew. Chem. Int. Ed. Engl. 1996, 35, 448-451;
181. l) H. Becher, K. B. Sharpless, Angew. Chem. 1996, 108, 447-449; Angew. Chem. Int. Ed. Engl. 1996, 35, 448-451;
182. m) C. Huart, L. Ghosez, ibid. 1997, 109, 627-629 and 1997, 36, 634-636;
183. m) C. Huart, L. Ghosez, ibid. 1997, 109, 627-629 and 1997, 36, 634-636;
184. n) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, ibid. 1996, 108, 103-105 and 1996, 35, 104-106;
185. n) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, ibid. 1996, 108, 103-105 and 1996, 35, 104-106;
186. o) Y. Kaida, Y. Okamoto, J.-C. Chambron, D. K. Mitchell, J.-P. Sauvage, Tetrahedron Lett. 1993, 34, 1019-1022;
187. p) F. Theil, H. Sonnenschein, T. Kreher, Tetrahedron: Asymmetry 1996, 7, 3365-3370;
188. q) K. D. Sugi, T. Nagata, T. Yamada, T. Kaiyama, Chem. Lett. 1996, 1081-1082;
189. r) C. Pepper, H. J. Smith, K. J. Barrell, P. J. Nicholls, M. J. E. Hewlins, Chirality 1994, 6, 400-404;
190. s) Y. Okamoto, R. Aburatani, K. Hatada, M. Honda, N. Inotsume, M. Nakano, J. Chromatogr. 1990, 513, 375-378.
191. J. Dingene in Chiral Separations by Liquid Chromatography (Ed.: G. Subramanian), VCH, New York, 1994, chap. 6, pp. 115-181.
192. Y. Okamoto, R. Aburatani, Y. Kaida, K. Hatada, Chem. Lett. 1988, 1125-1128.
193. a) K. Ikeda, T. Hamasaki, H. Kohno, T. Ogawa, T. Matsumoto, J. Sakai, Chem. Lett. 1989, 1089-1090;
194. b) A. Ishikawa, T. Shibata, J. Liq. Chromatogr. 1993, 16, 859-878.
195. a) Y. Kaida, Y. Okamoto, Bull. Chem. Soc. Jpn. 1992, 65, 2286-2288;
196. b) P. Petersson, K. E. Markides, J. Chromatogr. A 1994, 666, 381-394;
197. c) N. Bargmann-Leyder, A. Tambuté, M. Caude, Chirality 1995, 7, 311-325.
198. C. Minguillón, P. Franco, L. Oliveros, Pilar López, J. Chromatogr. A 1996, 728, 407-414.
199. a) N. Enomoto, S. Furukawa, Y. Ogasawara, H. Akano, Y. Kawamura, E. Yashima, Y. Okamoto, Anal. Chem. 1996, 68, 2789-2804;
200. b) A. Kamogawa, T. Fukui, Z. Nikuni, Z. Biochem. 1968, 63, 361-369.
201. a) Y. Kaida, Y. Okamoto, Bull. Chem. Soc. Jpn. 1993, 66, 2225-2232;
202. b) C. Chassaing, A. Thienpont, G. Félix, J. Chromatogr. A 1996, 738, 157-167.
203. a) S. J. Grieb, S. A. Matlin, A. M. Belenguer, H. J. Ritchie, J. Chromatogr. A 1995, 697, 271-278;
204. b) E. Yashima, P. Sahavattanpong, Y. Okamoto, Chirality 1996, 8, 446-451.
205. Y. Kaida, Y. Okamoto, J. Chromatogr. 1993, 641, 267-278.
206. T. Shimizu, Y. Yamazaki, H. Taka, N. Kamigata, J. Am. Chem. Soc. 1997, 119, 5966-5967.
207. a) Y. Kaida, Y. Okamoto, Chem. Lett. 1992, 85-88;
208. b) Y. Kaida, Y. Okamoto, Chirality 1992, 4, 122-124.
209. a) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Eng. 1988, 27, 1009-1020;
210. a) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Eng. 1988, 27, 1009-1020;
211. b) J.-M. Lehn, ibid. 1988, 100, 91 -116 and 1988, 27, 89-112;
212. b) J.-M. Lehn, ibid. 1988, 100, 91 - 116 and 1988, 27, 89-112;
213. c) Frontiers in Supramolecular Organic Chemistry and Photochemistry (Eds.: H.-J. Schneider, H. Dürr, J.-M. Lehn), VCH, Weinheim, 1988;
214. d) J. Rebek, Jr. Angew. Chem. 1990, 102, 261-272; Angew. Chem. Int. Ed. Eng. 1990, 29, 245-255;
215. d) J. Rebek, Jr. Angew. Chem. 1990, 102, 261-272; Angew. Chem. Int. Ed. Eng. 1990, 29, 245-255;
216. e) C. Seel, F. Vögtle, ibid. 1992, 104, 542-563 and 1992, 31 528-549;
217. e) C. Seel, F. Vögtle, ibid. 1992, 104, 542-563 and 1992, 31 528-549;
218. f) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395;
219. g) V. Böhmer, Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Eng. 1995, 34, 713-745;
220. g) V. Böhmer, Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Eng. 1995, 34, 713-745;
221. h) A. J. Kirby, ibid. 1996, 108, 770-790 and 1996, 35, 707-724;
222. h) A. J. Kirby, ibid. 1996, 108, 770-790 and 1996, 35, 707-724;
223. i) D. Philp, J. F. Stoddart, ibid. 1996, 108, 1242-1286 and 1996, 35, 1154-1196;
224. i) D. Philp, J. F. Stoddart, ibid. 1996, 108, 1242-1286 and 1996, 35, 1154-1196;
225. j) Y. Murakami, J. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721-758.
226. a) B. Feibush, A. Figueroa, R. Charles, K. D. Onan, P. Feibush, B. L. Karger, J. Am. Chem. Soc. 1986, 108, 3310-3318;
227. b) W. H. Pirkle, T. C. Pochapsky, ibid. 1986, 108, 5627-5628;
228. c) ibid. 1987, 109, 5975-5982;
229. d) G. Uccello-Barretta, C. Rosini, D. Pini, P. Salvadori, ibid. 1990, 112, 2707-2710;
230. e) K. B. Lipkowitz, S. Raghothama, J. Yang, ibid. 1992, 114, 1554-1562;
231. f) K. Lohmiller, E. Bayer, B. Koppenhoefer, J. Chromatogr. A 1993, 634, 65-77;
232. g) W. H. Pirkle, C. J. Welch, ibid. 1994, 683, 347-353;
233. h) W. H. Pirkle, P. G. Murray, D. J. Rausch, S. T. McKenna, J. Org. Chem. 1996, 61, 4769-4774.
234. a) K. B. Lipkowitz in A Practical Approach to Chiral Separations by Liquid Chromatography (Ed.: G. Subramanian), VCH, New York, 1994, chap. 2, pp. 19-55;
235. b) K. B. Lipkowitz, A. G. Anderson in Computational Approaches in Supramolecular Chemistry (Ed.: G. Wipff), Kluwer, Dordrecht, 1994, pp. 183-198;
236. c) K. B. Lipkowitz, J. Chromatogr. A 1995, 694, 15-37;
237. d) S. Topiol, M. Sabio, J. Moroz, W. B. Caldwell, J. Am. Chem. Soc. 1990, 110, 8367-8376;
238. e) K. B. Lipkowitz, G. Pearl, B. Coner, M. A. Peterson, ibid. 1997, 119, 600-610.
239. a) K. Oguni, A. Matsumoto, A. Isokawa, Polym. J. 1994, 26, 1257-1261;
240. b) T. C. Pinkerton, W. J. Howe, E. L. Ulrich, J. P. Comiskey, J. Haginaka, T. Murashima, W. F. Walkenhorst, W. M. Westler, J. L. Markley, Anal. Chem. 1995, 67, 2354-2367;
241. c) K. Oguni, M. Ito, A. Isokawa, A. Matsumoto, Chirality 1996, 8, 372-376.
242. a) E. Francotte, R. M. Wolf, D. J. Lohmann, J. Chromatogr. 1985, 347, 25-37;
243. b) T. Shibata, T. Sei, H. Nishimura, K. Deguchi, Chromatographia 1987, 24, 552-554;
244. c) A. J. Stipanovic, A. Sarko, Polymer 1978, 19, 3-8.
245. R. M. Wolf, E. Francotte, L. Glasser, I. Simon, H. A. Scheraga, Macromolecules 1992, 25, 709-720.
246. D. L. VanderHart, J. A. Hyatt, R. H. Attalla, V. C. Tirumalai, Macromolecules 1996, 29, 730-739
247. a) E. Francotte, R. M. Wolf, Chirality 1990, 2, 16-31;
248. b) R. Isaksson, P. Erandsson, L. Hansson, A. Holmberg, S. Berner, J. Chromatogr. 1990, 498, 257-280.
249. a) R. M. Wolf, E. Francotte, D. Lohmann, J. Chem. Soc. Perkin Trans. 2 1988, 893-901;
250. b) R. Isaksson, H. Wennerström, O. Wennerström, Tetrahedron 1988, 44, 1697-1705.
251. E. Francotte, G. Rihs, Chirality 1989, 1, 80-85.
252. C. M. Buchanan, J. A. Hyatt, D. W. Lowman, J. Am. Chem. Soc. 1989, 111, 7312-7319.
253. a) I. W. Wainer, M. C. Alembik, J. Chromatogr. 1986, 358, 85-93;
254. b) I. W. Wainer, M. C. Alembik, E. Smith, ibid. 1987, 388, 65-74;
255. c) I. W. Wainer, R. M. Stiffin, T. Shibata, ibid. 1987, 411, 139-151.
256. T. O'Brien, L. Crocker, R. Thompson, K. Thompson, P. H. Toma, D. A. Conlon, B. Feibush, C. Moeder, G. Bicker, N. Grinberg, Anal. Chem. 1997, 69, 1999-2007.
257. U. Vogt, P. Zugenmaier, Makromol. Chem. Rapid Commun. 1983, 4, 759-765.
258. J. Danhelka, M. Netopilik, M. Bohdanecky, J. Polym. Sci. Part B Polym. Phys. 1987, 25, 1801-1815.
259. a) E. Yashima, M. Yamada, Y. Okamoto, Chem. Lett. 1994, 579-582;
260. b) E. Yashima, M. Yamada, C. Yamamoto, M. Nakashima, Y. Okamoto, Enantiomer 1997, 2, 225-240.
261. a) W. B. Jennings, Chem. Rev. 1975, 75, 307-322;
262. b) M. T. Reetz, J. Rudolph, R. Mynott, J. Am. Chem. Soc. 1996, 118, 4494-4495.
263. E. Yashima, C. Yamamoto, Y. Okamoto, J. Am. Chem. Soc. 1996, 118, 4036-4048.
264. E. Yashima, C. Yamamoto, Y. Okamoto, unpublished results.
265. E. Yashima, M. Yamada, Y. Kaida, Y. Okamoto, J. Chromatogr. A 1995, 694, 347-354.
266. C. Yamamoto, M. Yamada, E. Yashima, Y. Okamoto, Polym. Prep. Jpn. 1995, 44, 3029-3030.
267. a) C. F. Fan, B. D. Olafson, M. Blanco, S. L. Hsu, Macromolecules 1992, 25, 3667-3676;
268. b) D. N. Theodorou, U. W. Suter, ibid. 1985, 18, 1467-1478.
269. a) A. Tsuboi, M. Yamasaki, T. Norisue, A. Teramoto, Polym. J. 1995, 27, 1219-1229;
270. b) A. Tsuboi, T. Norisue, A. Teramoto, Macromolecules 1996, 29, 3597-3602.
271. a) Y. Okamoto, M. Kawashima, K. Hatada, J. Am. Chem. Soc. 1984, 106, 5357-5359;
272. b) Y. Okamoto, J. Noguchi, E. Yashima, Reactive Polym. Functional Polym. 1998, in press;
273. c) Q. B. Cass, A. L. Bassi, S. A. Matlin, Chirality 1996, 8, 131-135;
274. d) G. Félix, T. Zhang, J. Chromatogr. A 1993, 639, 141-149.
275. a) R. Aburatani, Y. Okamoto, K. Hatada, Bull. Chem. Soc. Jpn. 1990, 63, 3606-3610;
276. b) E. Yashima, P. Sahavattanapong, C. Yamamoto, Y. Okamoto, Bull. Chem. Soc. Jpn. 1997, 70, 1977-1984;
277. c) O. Weller, J. Schulze, W. König, J. Chromatogr. A 1987, 403, 263-270;
278. d) A. M. Stalcup, K. L. Williams, ibid. 1995, 695, 185-193.
279. a) A. Sarko, A. Biloski, Carbohydr. Res. 1980, 79, 11-21;
280. b) F. H. Allen, O. Kennard, Chemical Design Automation News 1993, 8, 31.
281. T. D. Booth, I. W. Wainer, J. Chromatogr. A 1996, 737, 157-169.
282. a) S. Li, W. C. Purdy, Chem. Rev. 1992, 92, 1457-1470;
283. b) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Eng. 1994, 33, 803-822.
284. b) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Eng. 1994, 33, 803-822.
285. a) T. Hargitai, Y. Okamoto, J. Liq. Chromatogr. 1993, 16, 843-858;
286. b) T. Hargitai, Y. Kaida, Y. Okamoto, J. Chromatogr. 1993, 628, 11-22.
287. T. Steiner, G. Koellner, J. Am. Chem. Soc. 1994, 116, 5122-5128.
288. E. Yashima, J. Noguchi, Y. Okamoto, Chem. Lett. 1992, 1959-1962.
289. E. Yashima, J. Noguchi, Y. Okamoto, J. Applied Polym. Sci. 1994, 54, 1087-1091.
290. E. Yashima, J. Noguchi, Y. Okamoto, Tetrahedron: Asymmetry 1995, 6, 1889-1890.
291. a) M. Newcomb, J. L. Toner, R. C. Helgeson, D. J. Cram, J. Am. Chem. Soc. 1979, 101, 4941-4947;
292. b) T. Yamaguchi, K. Nishimura, T. Shinbo, M. Sugiura, Chem. Lett. 1985, 1549-1552;
293. c) W. H. Pirkle, E. M. Doherty, J. Am. Chem. Soc. 1989, 111, 4113-4114;
294. d) W. H. Pirkle, W. E. Bowen, Tetrahedron: Asymmetry 1994, 5, 773-776.
295. a) N. Ogata, Mcromol. Symp. 1995, 543-559;
296. b) T. Aoki, K. Shinohara, T. Kaneko, E. Oikawa, Macromolecules 1996, 29, 4192-4198;
297. c) M. Yoshikawa, J. Izumi, S. Sakamoto, ibid. 1996, 29, 8197-8203;
298. d) K. Inoue, A. Miyahara, T. Itaya, J. Am. Chem. Soc. 1997, 119, 6191-6192.
299. a) E. Yashima, J. Noguchi, Y. Okamoto, Macromolecules 1995, 28, 8368-8374;
300. b) Y. Okamoto, H. Sakamoto, K. Hatada, M. Irie, Chem. Lett. 1986, 983-986.
301. a) G. Bredig, F. Gerstner, Biochem. Z. 1932, 250, 414-429;
302. b) Y. Kawabata, M. Tanaka, I. Ogata, Chem. Lett. 1976, 1213-1214;
303. c) T. V. RajanBabu, T. A. Ayers, A. L. Casalnouvo, J. Am. Chem. Soc. 1994, 116, 4101-4102.
304. a) S. Kataoka, T. Ando, Kobunshi Ronbunshu 1980, 37, 185-190;
305. b) Polymer 1984, 25, 507-510.
306. Coated-type, cellulose-based CSPs are available from Daicel: triacetate (17, Chiralcel OA), tribenzoate (24, Chiralcel OB), tris(4-methylbenzoate) (21, Chiralcel OJ), tricinnamate (Chiralcel OK), trisphenylcarbamate (40, Chiralcel OC), tris(4-methylphenylcarbamate) (34, Chiralcel OG), tris(4-chlorophenylcarbamate) (42, Chiralcel OF), tris(3,5-dimethylphenylcarbamate) (49, Chiralcel OD). Microcrystalline CTA-I (17) is also available from Daicel (Chiralcel CA-I), Merck (Cellulose triacetate), and Macherey-Nagel (Cellulose Ce-AC-40XF). Coated-type, amylose-based CSPs are commercialized from Daicel: tris(3,5-dimethylphenylcarbamate) (78, Chiralpak AD), tris((S)-1-phenylethylcarbamate) (89, Chiralpak AS).
307. a) J. Dingene, J. N. Kinkei, J. Chromatogr. 1994, 666, 627-650;
308. b) R.-M. Nicoud, G. Fuchs, P. Adam, M. Baily, E. Küsters, F. D. Antia, R. Reuille, E. Schmid, Chirality 1993, 5, 267-271;
309. c) M. Negawa, F. Shoji, J. Chromatogr. 1992, 590, 113-117.