Molecular recognition study on supramolecular systems. 20. Molecular recognition and enantioselectivity of aliphatic alcohols by L-tryptophan- modified β-cyclodextrin

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1487-1493

  Liu, Yu ^a,b   Han, Bao Hang ^b,c   Sun, Shi Xin ^b   Wada, Takehiko ^c   Inoue, Yoshihisa ^a,c  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NANKAI UNIVERSITY   (China)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BETA CYCLODEXTRIN; INDOLE DERIVATIVE; TRYPTOPHAN;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; HYDROPHOBICITY; ISOMERISM; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; SYNTHESIS;

EID: 0033525501     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981891k     Document Type: Article

References (38)

1. (a) Hamilton, A. D. Tetrahedron 1995, 51, 343-648.
2. (b) Gokel, G. W. Comprehensive Supramolecular Chemistry, Volume 1: Molecular Recognition: Receptors for Cationic Guests; Pergamon Press: Oxford, U.K., 1996.
3. (c) Vögtle, F. Comprehensive Supramolecular Chemistry, Volume 2: Molecular Recognition: Receptors for Molecular Guests; Pergamon Press: Oxford, U.K., 1996.
4. Gellman, S. H. Chem. Rev. 1997, 97, 1231-1734.
5. Szejtli, J. Cyclodextrin and their Inclusion Complexation; Akademia Kiado: Budapest, 1982.
6. Saenger, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 344-362.
7. Wenz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 803-822.
8. Connors, K A. Chem. Rev. 1997, 97, 1325-1357.
9. Croft, A. P.; Bartsch, R. A. Tetrahedron 1983, 39, 1417-1474.
10. (a) Breslow, R. Science 1982, 218, 532-537.
11. (b) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
12. (a) Tabushi, I. Acc. Chem. Res. 1982, 15, 66-72.
13. (b) Tabushi, I. Tetrahedron 1984, 40, 269-292.
14. (a) Liu, Y.; Li, B.; Han, B.-H.; Li, Y.-M.; Chen, R.-T. J. Chem. Soc., Perkin Trans. 2 1997, 1275-1278.
15. (b) Liu, Y.; Zhang, Y.-M.; Sun, S.-X.; Zhang, Z.-H.; Chen, Y.-T. Acta Chim. Sin. (Huaxue Xuebao) 1997, 55, 779-785.
16. (a) Hamasaki, K.; Ikeda, H.; Nakamura, A.; Ueno, A.; Toda, F.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1993, 115, 5035-5040.
17. (b) Wang, Y.; Ikeda, T.; Ikeda, H.; Ueno, A.; Toda, F. Bull. Chem. Soc. Jpn. 1994, 67, 1598-1607.
18. (c) Ikeda, H.; Nakamura, M.; Ise, N.; Oguma, N.; Nakamura, A.; Ikeda, T.; Toda, F.; Ueno, A. J. Am. Chem. Soc. 1996, 118, 10980-10988.
19. (d) Matsushita, A.; Kuwabara, T.; Nakamura, A.; Ikeda, H.; Ueno, A. J. Chem. Soc., Perkin Trans. 2 1997, 1705-1710.
20. Corradini, R.; Dossena, A.; Galaverna, G.; Marchelli, R.; Panagia, A.; Sartor, G. J. Org. Chem. 1997, 62, 6283-6289.
21. Lipkowitz, K. B.; Raghothama, S.; Yang, J.-a. J. Am. Chem. Soc. 1992, 114, 1554-1562.
22. Liu, Y.; Han, B.-H.; Li, B.; Zhang, Y.-M.; Zhao, P.; Chen, Y.-T.; Wada, T.; Inoue, Y. J. Org. Chem. 1998, 63, 1444-1454.
23. (a) Matsui, Y.; Okimoto, A. Bull. Chem. Soc. Jpn. 1978, 51, 3030-3034.
24. (b) Matsui, Y.; Ogawa, K.; Mikami, S.; Yoshimoto, M.; Mochida, K. Bull. Chem. Soc. Jpn. 1989, 62, 1219-1223.
25. (c) Matsui, Y.; Fujie, M.; Hanaoka, L. Bull. Chem. Soc. Jpn. 1989, 62, 1451-1457.
26. Kajtár, M.; Horváth-Toró, C.; Kuthi, É.; Szejtli, J. Acta Chim. Acad. Sci. Hung. 1982, 110, 327-355.
27. The assumption is valid for the host L-Trp-β-CD existing in either one conformer or two conformers; see ref 11b.
28. Tong, L.-H.; Hou, Z.-J.; Inoue, Y.; Tai, A. J. Chem. Soc., Perkin Trans. 2 1982, 1253-1257.
29. Inoue, Y.; Yamamoto, K.; Wada, T.; Everitt, S.; Gao, X.-M.; Hou, Z.-J.; Tong, L.-H.; Jiang, S.-K., Wu, H.-M. J. Chem. Soc., Perkin Trans. 2 1998, 1807-1816.
30. (a) Harrison, J. C.; Eftink, M. R. Biopolymers 1982, 21, 1153-1166.
31. (b) Cromwell, W. C.; Bystrom, K.; Eftink, M. R. J. Phys. Chem. 1985, 89, 326-332.
32. (c) Eftink, M. R.; Andy, M. L.; Bystrom, K.; Perlmutter, H. D.; Kristol, D. S. J. Am. Chem. Soc. 1989, 111, 6765-6772.
33. (a) Harata, K. Bull. Chem. Soc. Jpn. 1975, 48, 2409-2413.
34. (b) Harata, K. Bull. Chem. Soc. Jpn. 1977, 50, 1416-1424.
35. (c) Harata, K.; Uedaira, H.; Tanaka, J. Bull. Chem. Soc. Jpn. 1978, 51, 1627-1634.
36. (d) Harata, K. Bull. Chem. Soc. Jpn. 1980, 53, 2782-2786.
37. Liu, Y.; Han, B.-H.; Qi, A.-D.; Chen, R.-T. Bioorg. Chem. 1997, 25, 155-162.
38. Liu, Y.; Zhang, Y.-M.; Sun, S.-X.; Li, Y.-M.; Chen, R.-T. J. Chem. Soc., Perkin Trans. 2 1997, 1609-1613.