Catalysis of the enolization of indan-2-one by cyclodextrins in aqueous solution

Journal of the Chemical Society. Perkin Transactions 2

Volumn 1996, Issue 12, 1996, Pages 2763-2769

  Tee, Oswald S ^a   Donga, Robert A ^a  

^a Gina Cody School of Engineering and Computer Science   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042574007     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29960002763     Document Type: Article

References (56)

1. (a) M. Bender and M. Komiyama, Cyclodextrin Chemistry, Springer Verlag, New York. 1978;
2. (b) J. Szejtli, Cyclodextrins and their Inclusion Complexes, Akademial Kiado, Budapest, 1982.
3. (a) J. Szejtli, Cydodextrin Technology, Kluwer, Dordrecht, 1988;
4. (b) J. F. Stoddart and R. Zarzycki, Recl. Trav. Chim. Pays-Bas, 1988, 107, 515;
5. (c) G. Wenz. Angew. Chem., Inf. Ed. Engl., 1994, 33, 803.
6. (a) J. H. Fendler and E. J. Fendler, Catalysis in Micellar and Macro-molecular Systems, Academic Press, New York, 1975;
7. (b) C. Sirlin, Bull. Soc. Chim. Fr., 1984, II-5;
8. (c) M. Komiyama and M. L. Bender, in The Chemistry of Enzyme Action, ed. M. I. Page, Elsevier, Amsterdam, 1984.
9. (a) O. S. Tee, Carbohydr. Res., 1989, 192, 181;
10. (b) O. S. Tee, Adv. Phys. Org. Chem., 1994, 29, 1.
11. (a) R. L. Van Etten, J. F. Sebastian, G. A. Clowes and M. L. Bender, J. Am. Chem. Soc., 1967, 89, 3242;
12. (b) R. L. Van Etten, G. A. Clowes, J. F. Sesbastian and M. L. Bender, J. Am. Chem. Soc., 1967, 89, 3253;
13. (c) D. W. Griffiths and M. L. Bender, Adv. Catalysis, 1973, 23, 209;
14. (d) M. Komiyama and M. L. Bender, J. Am. Chem. Soc., 1978, 100, 4576; Bull. Chem. Soc. Jpn., 1980, 53, 1073;
15. (d) M. Komiyama and M. L. Bender, J. Am. Chem. Soc., 1978, 100, 4576; Bull. Chem. Soc. Jpn., 1980, 53, 1073;
16. (e) R. Breslow, Adv. Enzymol., 1986, 58, 1;
17. (f) Y. Matsui, T. Nishioka and T. Fujita, Top. Curr: Chem., 1985, 128, 61;
18. (g) O. S. Tee and B. K. Takasaki, Can. J. Chem., 1985, 63, 3540;
19. (h) O. S. Tee, C. Mazza and X.-X. Du, J. Org. Chem., 1990, 55, 3603;
20. (i) O. S. Tee and X.-X. Du, J. Am. Chem. Soc., 1992, 114, 620;
21. (j) T. A. Gadosy and O. S. Tee, J. Chem. Soc., Perkin Trans. 2, 1994, 715;
22. (k) O. S. Tee and T. A. Gadosy, J. Chem. Soc., Perkin Trans. 2, 1994, 2191;
23. O. S. Tee and M. J. Boyd, J. Chem. Soc., Perkin Trans. 2, 1995, 1237.
24. M. Komiyama and S. Inoue, Bull. Chem. Soc. Jpn., 1980, 53, 3334.
25. V. Daffe and J. Fastrez, J. Chem. Soc., Perkin Trans. 2, 1983, 789.
26. X. Cheng, X. Jiang, J. Gu and Y. Shen, Acta Chim. Sin. (Engl. Ed.), 1985, 84.
27. O. S. Tee, N. R. Iyengar and B. K. Takasaki, Can. J. Chem., 1993, 71, 2139.
28. (a) A. M. Ross, D. L. Whalen, S. Eldin and R. M. Pollack, J. Am. Chem. Soc., 1988, 110, 1981;
29. (b) J. R. Keeffe, A. J. Kresge and Y. Yin, J. Am. Chem. Soc., 1988, 110, 1982;
30. (c) J. R. Keeffe, A. J. Kresge and Y. Yin, J. Am. Chem. Soc., 1988, 110, 8201.
31. (a) R. I. Gelb, L. M. Schwartz, J. J. Bradshaw and D. A. Laufer, Bioorg. Chem., 1980, 9, 299;
32. (b) R. I. Gelb, L. M. Schwartz and D. A. Laufer, Bioorg. Chem., 1982, 11, 274.
33. (a) A. P. Croft and R. A. Bartsch, Tetrahedron, 1983, 39, 1417;
34. (b) J. Szejtli, Carbohydrate Polymers, 1990, 12, 375.
35. C. H. Arrowsmith, A. J. Kresge and Y. C. Tang, J. Am. Chem. Soc., 1991, 113, 179.
36. A. Fersht, Enzyme Structure and Mechanism, Freeman, New York, 2nd edn., 1985.
37. (a) O. S. Tee and J. J. Hoeven, J. Am. Chem. Soc., 1989, 111, 8318;
38. (b) O. S. Tee, M. Bozzi, J. J. Hoeven and T. A. Gadosy, J. Am. Chem. Soc., 1993, 115, 8990;
39. (c) O. S. Tee and M. Bozzi, J. Am. Chem. Soc., 1990, 112, 7815;
40. (d) O. S. Tee, M. Bozzi, N. Clement and T. A. Gadosy, J. Org. Chem., 1995, 60, 3509;
41. (e) T. A. Gadosy and O. S. Tee, Can J. Chem., 1996, 74, 745.
42. (a) J. Emert and R. Breslow, J. Am. Chem. Soc., 1975, 97, 670;
43. (b) R. Breslow, M. F. Czarniecki, J. Emert and H. Hamaguchi, J. Am. Chem. Soc., 1980, 102, 762;
44. (c) K. Fujita, A. Shinoda and T. Imoto, J. Am. Chem. Soc., 1980, 102, 1161.
45. K. Harata and H. Uedaira, Bull. Chem. Soc. Jpn., 1975, 48, 375.
46. (a) A. J. Kirby, Adv. Phys. Org. Chem., 1980, 17, 183;
47. (b) A. J. Kirby, Chem., Int. Ed. Engl., 1996, 35, 707.
48. (a) J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1988, 27, 89;
49. (b) H.-J. Schneider and H. Dürr, Frontiers in Supramolecular Organic Chemistry and Photochemistry, VCH, Weinheim, 1990;
50. (c) F. Vögtle, Supramolecular Chemistry, Wiley, Chichester, 1991.
51. (a) J. L. Kurz, J. Am. Chem. Soc., 1963, 85, 987; Acc. Chem. Res., 1972, 5, 1;
52. (a) J. L. Kurz, J. Am. Chem. Soc., 1963, 85, 987; Acc. Chem. Res., 1972, 5, 1;
53. (b) G. E. Lienhard, Science (Washington. D. C.), 1988, 180, 149;
54. (c) J. Kraut, Science (Washington, D. C.), 1988, 242, 533.
55. (a) O. S. Tee and T. A. Gadosy, J. Chem. Soc., Perkin Trans. 2, 1994, 2307;
56. (b) T. A. Gadosy and O. S. Tee, J. Chem. Soc., Perkin Trans. 2, 1995, 71.