Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1058-1063

  Ponde, Datta E ^a   Deshpande, Vishnu H ^a   Bulbule, Vivek J ^a   Sudalai, Ammugam ^a   Gajare, Anil S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000362753     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971404l     Document Type: Article

References (47)

1. Otera, J. Chem. Rev. (Washington, D.C.) 1993, 93, 1449-1470.
2. Yazawa, H.; Tanaka, K.; Kariyone, K. Tetrahedron Lett. 1974, 3995-3996.
3. Blossey, E. C.; Turner, L. M.; Neckers, D. C. Tetrahedron Lett. 1973, 1823-26.
4. (a) Rehberg, C. E.; Fisher, C. H. J. Am. Chem. Soc. 1944, 66, 1203-1207.
5. (b) Rehberg, C. E.; Faucette, W. A.; Fisher, C. H. J. Am. Chem. Soc. 1944, 66, 1723-1724.
6. (c) Rehberg, C. E. Organic Synthesis; Wiley: New York, 1955; Collect Vol. 3, pp 146-148.
7. (d) Haken, J. K. J. Appl. Chem. 1963, 13, 168-171.
8. (a) Taft, R. W., Jr.; Newman, M. S.; Verhoek, F. H. J. Am. Chem. Soc. 1950, 72, 4511-4519.
9. (b) Billman, J. H.; Smith, W. T., Jr.; Rendall, J. L. J. Am. Chem. Soc. 1947, 69, 2058-2059.
10. (a) Osipow, L.; Snell, F. D.; York, W. C.; Finchler, A. Ind. Eng. Chem. 1956, 48, 1459-1462.
11. (b) Osipow, L.; Snell, F. D.; Finchler, A. J. Am. Oil Chem. Soc. 1957, 34, 185-188.
12. (c) Komori, S.; Okahara, M.; Okamoto, K. J. Am. Oil Chem. Soc. 1960, 37, 468-473.
13. Otera, J.; Yano, T.; Kawabata, A.; Nozaki, H., Tetrahedron Lett. 1986, 27, 2383-2386.
14. Seebach, D.; Hungerbuhler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Zuger, M. Synthesis 1982, 138-141.
15. Taber, D. F.; Amedio, J. Jr.; Patel, Y. J. Org. Chem. 1985, 50, 3618-3619.
16. Chavan, S. P.; Zubaida, P. K.; Dantale, S. W.; Keshavaraja, A.; Ramaswamy, A. V.; Ravindranathan, T. Tetrahedron Lett. 1996, 37, 233-236.
17. Balaji, B. S.; Sasidharan, M.; Kumar, R.; Chanda, B. J. Chem. Soc., Chem. Commun. 1996, 707-708.
18. (a) Posner G. H.; Oda, M. Tetrahedron Lett. 1981, 22, 5003-5006.
19. (b) Rana, S. S.; Barlow, J. J.; Matta, K. L. Tetrahedron Lett. 1981, 22, 5007-5010.
20. (c) Posner, G. H.; Okada, S. S.; Babiak, K. A.; Miura, K.; Rose, K. K. Synthesis 1981, 11, 789-790.
21. Laszlo, P. Pure Appl. Chem. 1990, 62, 2027-2030.
22. Laszlo, P. Science 1987, 235, 1473-1477.
23. Cornelis, A.; Laszlo, P. Synth. Lett. 1994, 155-161.
24. Ponde, D.; Borate, H. B.; Sudalai, A.; Ravindranathan, T.; Deshpande, V. H. Tetrahedron Lett. 1996, 37, 4605-4608.
25. Upadhya, T. T.; Daniel, T.; Sudalai, A.; Ravindranathan, T.; Sabu, K. R. Synth. Commun. 1996, 26, 4539-4544.
26. Benetti, S.; Romagnoli, R.; De risi, C.; Spalluto, G.; Zanirato, V. Chem. Rev. (Washington, D.C.) 1995, 95, 1065-1114.
27. Ahmad, S.; Iqbal, J. Tetrahedron Lett. 1986, 27, 3791-3794.
28. (a) Lopez-Alvarado, P.; Avendano, C.; Menendez, J. C. Synth. Commun. 1992, 22, 2329-2333.
29. (b) Kobuke, Y.; Yoshida, J. Tetrahedron Lett. 1978, 367-370.
30. (c) Yaggi, N. F.; Douglas, K. T. J. Chem. Soc., Chem. Commun. 1977, 609-610.
31. (d) Booth, P. M.; Fox, C. N. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1987, 121-129.
32. (e) Sakaki, J.; Kobayashi, S.; Sato, M.; Kaneko, C. Chem. Pharm. Bull. 1990, 38, 2262-2264.
33. (a) Staab, H. Angew. Chem., Int. Ed. Engl. 1962, 1, 351
34. (b) Lemieux, R. U. Driguez, H. J. Am. Chem. Soc. 1975, 97, 4063-4069.
35. (c) Vernon, J.; Roseman, S.; Lee, Y. C. Carbohydr. Res. 1980, 82, 59.
36. Mukaiyama, T.; Pai, F. C.; Onaka, M.; Narasaka, K. Chem. Lett. 1980, 563-566.
37. Olah, G. A.; Narang, S. C.; Salem, G. F. Gupta, B. G. B. Synthesis 1981, 142-143.
38. Mitsunobu, O. Synthesis 1981, 1-28 and references therein.
39. Kocienski, P. J. Protective Groups; Enders, D., Noyori, R., Trost, B. M., Eds.; George Thieme Verlag: Stuttgart, New York, 1994. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; J. Wiley: New York, 1991.
40. Kocienski, P. J. Protective Groups; Enders, D., Noyori, R., Trost, B. M., Eds.; George Thieme Verlag: Stuttgart, New York, 1994. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; J. Wiley: New York, 1991.
41. Grobel, B. T.; Seebach, D. Synthesis 1977, 357-402.
42. Kamitori, Y.; Hojo, M.; Masuda, R.; Kimura, J.; Yoshida, T. J. Org. Chem. 1986, 51, 1427-1431.
43. Kumar, P.; Reddy, R. S.; Singh, A. P.; Pandey, B. Tetrahedron Lett. 1992, 33, 825-826.
44. Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24, 169-172.
45. Villemin, D.; Labiad, B.; Hammadi, M. J. Chem. Soc., Chem. Commun. 1992, 1192-1193.
46. Tateiwa, J.; Horiuchi, H.; Uemura, S. J. Org. Chem. 1995, 60, 4039-4043.
47. Sabu, K. R.; Sukumar, R.; Lalithambika, M. Bull. Chem. Soc. Jpn. 1993, 66, 3535-3541.