Tris(cyclohexylcarbamate)s of cellulose and amylose as potential chiral stationary phases for high-performance liquid chromatography and thin-layer chromatography

Journal of the American Chemical Society

Volumn 122, Issue 17, 2000, Pages 4056-4059

  Kubota, Takateru ^a   Yamamoto, Chiyo ^a   Okamoto, Yoshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMYLOSE; CARBAMIC ACID DERIVATIVE; CELLULOSE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET RADIATION;

EID: 0034600248     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992421q     Document Type: Article

References (46)

1. (a) Okamoto, Y.; Kawashima, M.; Hatada, K. J. Am. Chem. Soc. 1984, 106, 5357.
2. (b) Okamoto, Y.; Kawashima, M.; Hatada, K. J. Chromatogr. 1986, 363, 173.
3. (c) Okamoto, Y.; Aburatani, R.; Fukumoto, T.; Hatada, K. Chem. Lett. 1987, 1857.
4. (d) Okamoto, Y.; Aburatani, R.; Hatano, K.; Hatada, K. J. Liq. Chromatogr. 1988, 11, 2147.
5. (e) Oguni, K.; Oda, H.; Ichida, A. J. Chromatogr. A 1995, 694, 91.
6. (f) Allenmark, S. G. Chromatographic Enantioseparation; Ellis Horwood: Chichester, 1988.
7. (g) Francotte, E. J. Chromatogr. A 1992, 576, 1.
8. (h) Francotte, E. J. Chromatogr. A 1994, 666, 565.
9. For reviews: (a) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020. (b) Yashima, E.; Yamamoto, C.; Okamoto, Y. Synlett 1998, 344. (c) Yashima, E.; Okamoto, Y. Bull. Chem. Soc. Jpn. 1995, 68, 3289. (d) Okamoto, Y.; Kaida, Y. J. Chromatogr. A 1994, 666, 403. (e) Ishikawa, A.; Shibata, T. J. Liq. Chromatogr. 1993, 16, 859.
10. For reviews: (a) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020. (b) Yashima, E.; Yamamoto, C.; Okamoto, Y. Synlett 1998, 344. (c) Yashima, E.; Okamoto, Y. Bull. Chem. Soc. Jpn. 1995, 68, 3289. (d) Okamoto, Y.; Kaida, Y. J. Chromatogr. A 1994, 666, 403. (e) Ishikawa, A.; Shibata, T. J. Liq. Chromatogr. 1993, 16, 859.
11. For reviews: (a) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020. (b) Yashima, E.; Yamamoto, C.; Okamoto, Y. Synlett 1998, 344. (c) Yashima, E.; Okamoto, Y. Bull. Chem. Soc. Jpn. 1995, 68, 3289. (d) Okamoto, Y.; Kaida, Y. J. Chromatogr. A 1994, 666, 403. (e) Ishikawa, A.; Shibata, T. J. Liq. Chromatogr. 1993, 16, 859.
12. For reviews: (a) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020. (b) Yashima, E.; Yamamoto, C.; Okamoto, Y. Synlett 1998, 344. (c) Yashima, E.; Okamoto, Y. Bull. Chem. Soc. Jpn. 1995, 68, 3289. (d) Okamoto, Y.; Kaida, Y. J. Chromatogr. A 1994, 666, 403. (e) Ishikawa, A.; Shibata, T. J. Liq. Chromatogr. 1993, 16, 859.
13. For reviews: (a) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020. (b) Yashima, E.; Yamamoto, C.; Okamoto, Y. Synlett 1998, 344. (c) Yashima, E.; Okamoto, Y. Bull. Chem. Soc. Jpn. 1995, 68, 3289. (d) Okamoto, Y.; Kaida, Y. J. Chromatogr. A 1994, 666, 403. (e) Ishikawa, A.; Shibata, T. J. Liq. Chromatogr. 1993, 16, 859.
14. (a) Yashima, E.; Yamamoto, C.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 4036.
15. (b) Yashima, E.; Yamada, M.; Okamoto, Y. Chem. Lett. 1994, 579.
16. (c) Yashima, E.; Yamada, M.; Yamamoto, C.; Nakashima, M.; Okamoto, Y. Enantiomer 1997, 2, 225.
17. (d) Yashima, E.; Yamada, M.; Kaida, Y.; Okamoto, Y. J. Chromatogr. A 1995, 694, 347.
18. (e) Lipkowitz, K. B. In A Practical Approach to Chiral Separations by Liquid Chromatography; Subramanian, G., Ed.; VCH: New York, 1994; Chapter 2.
19. (f) Lipkowitz, K. B.; Anderson, A. G. In Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwer: Dordrecht, 1994.
20. (g) Lipkowitz, K. B. J. Chromatogr. A 1995, 694, 15.
21. (h) Topiol, S.; Sabio, M.; Moroz, J.; Caldwell, W. B. J. Am. Chem. Soc. 1990, 110, 8367.
22. Lipkowitz, K. B.; Pearl, G.; Coner, B.; Peterson, M. A. J. Am. Chem. Soc. 1997, 119, 600.
23. (j) Yamamoto, C.; Yamada, M.; Yashima, E.; Okamoto, Y. Polym. Prepr. Jpn. 1995, 44, 3029.
24. (k) Yamamoto, C.; Yashima, E.; Okamoto, Y. Bull. Chem. Soc. Jpn, 1999, 72, 1815.
25. (a) Pirkle, W. H.; Finn, J. M.; Schreiner, J. L.; Hamper, B. C. J. Am. Chem. Soc. 1981, 103, 3964.
26. (b) Welch, C. J. Adv. Chromatogr. 1995, 35, 171.
27. (c) Shinbo, T.; Yamaguchi, T.; Nishimura, K.; Sugiura, M. J. Chromatogr. A 1987, 405, 145.
28. (d) Chang, S. C.; Reid, G. L., III; Chang, C, D.; Armstrong, D. W. Trends Anal. Chem. 1993, 12, 144.
29. (e) Blaschke, G. Angew. Chem., Int. Ed. Engl. 1980, 19, 13.
30. (f) Blaschke, G. J. Liq. Chromatogr. 1986, 9, 341.
31. (g) Okamoto, Y.; Okamoto, I.; Yuki, H.; Murata, S.; Noyori, R.; Takaya, H. J. Am. Chem. Soc. 1981, 103, 6971.
32. (h) Okamoto, Y.; Hatada, K. J. Liq. Chromatogr. 1986, 9, 369.
33. (i) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349.
34. (j) Hermansson, J.; Eriksson, M. J. Liq. Chromatogr. 1986, 9, 621.
35. (k) Allenmark, S. G. J. Liq. Chromatogr. 1986, 9, 425.
36. (l) Miwa, T.; Miyakawa, T. J. Chromatogr. 1987, 408, 316.
37. (m) Erlandsson, P.; Marie, I.; Hansson, L.; Isaksson, R.; Pettersson, C.; Pettersson, G. J. Am. Chem. Soc. 1990, 112, 4573.
38. (n) Wainer, I. W.; Jadaud, P.; Schombaum, G. R.; Kadadker, S. V.; Henry, M. P. Chromatographia 1988, 25, 903.
39. (o) Noctor, T.; Felix, G.; Wainer, I. W. Chromatographia 1991, 31, 55.
40. (p) Haginaka, J.; Murashima, T.; Seyama, C. J. Chromatogr. A 1994, 666, 203.
41. Kaida, Y.; Okamoto, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2286.
42. Koller, H.; Rimböck, K.-H.; Mannschreck, A. J. Chromatogr. 1983, 282, 89.
43. Commercial name: Chiralcel OD (Daicel).
44. Commercial name: Chiralpak AD (Daicel).
45. (a) Bhushan, R.; Parshad, V. J. Chromatogr. A 1996, 736, 235.
46. (b) Armstrong, D. W.; Zhou, Y. J. Liq. Chromatogr. 1994, 17, 1695.