One-pot transformation of p-toluenesulfonates of 2,3-epoxy alcohols into allylic alcohols

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8307-8310

  Habashita, Hiromu ^a   Kawasaki, Takeshi ^a   Akaji, Masako ^a   Tamamura, Hirokazu ^a   Kimachi, Tetsutaro ^a   Fujii, Nobutaka ^a   Ibuka, Toshiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL ALCOHOL; AMMONIUM CHLORIDE; BENZENESULFONIC ACID DERIVATIVE; EPOXIDE; PHOSPHINE DERIVATIVE; POTASSIUM IODIDE; SOLVENT; TOLUENESULFONIC ACID DERIVATIVE; ZINC;

ARTICLE; CHEMICAL REACTION; IODINATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 0030702856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10208-8     Document Type: Article

References (38)

1. Chem. Eng. News 1995, Sept. 11, 27.
2. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370. Adam, W.; Peters, K.; Renz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1107. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197. Evans, P. A.; Holmes, A. B.; Russell, K. J. Chem. Soc., Perkin Trans. 1, 1994, 3397. Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. Banwell, M. G.; Bui, C. T.; Hockless, D. C. R.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1, 1997, 1261.
3. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370. Adam, W.; Peters, K.; Renz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1107. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197. Evans, P. A.; Holmes, A. B.; Russell, K. J. Chem. Soc., Perkin Trans. 1, 1994, 3397. Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. Banwell, M. G.; Bui, C. T.; Hockless, D. C. R.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1, 1997, 1261.
4. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370. Adam, W.; Peters, K.; Renz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1107. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197. Evans, P. A.; Holmes, A. B.; Russell, K. J. Chem. Soc., Perkin Trans. 1, 1994, 3397. Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. Banwell, M. G.; Bui, C. T.; Hockless, D. C. R.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1, 1997, 1261.
5. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370. Adam, W.; Peters, K.; Renz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1107. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197. Evans, P. A.; Holmes, A. B.; Russell, K. J. Chem. Soc., Perkin Trans. 1, 1994, 3397. Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. Banwell, M. G.; Bui, C. T.; Hockless, D. C. R.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1, 1997, 1261.
6. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370. Adam, W.; Peters, K.; Renz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1107. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197. Evans, P. A.; Holmes, A. B.; Russell, K. J. Chem. Soc., Perkin Trans. 1, 1994, 3397. Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. Banwell, M. G.; Bui, C. T.; Hockless, D. C. R.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1, 1997, 1261.
7. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370. Adam, W.; Peters, K.; Renz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1107. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197. Evans, P. A.; Holmes, A. B.; Russell, K. J. Chem. Soc., Perkin Trans. 1, 1994, 3397. Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. Banwell, M. G.; Bui, C. T.; Hockless, D. C. R.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1, 1997, 1261.
8. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
9. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
10. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
11. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
12. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
13. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
14. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
15. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
16. Polson, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579. Polson, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31. 5603. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004. Kumar, A.; Dittmer, D. C. Tetrahedron Lett. 1994, 35, 5583. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311. Kumar, A.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4760. See also, Xu, Q.; Chao, B.; Wang, Y.; Dittmer, D. C. Tetrahedron 1997, 53, 12131.
17. Yasuda, A.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1757.
18. Yadav, J. S.; Shekharam, T.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1990, 843. Yadav, J. S.; Srinivas, D.; Shekharam, T. Tetrahedron Lett. 1994, 35, 3625. See also, RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986. Gurjar, M. K.; Henri, J. T., Jr.; Bose, D. S.; Rao, A. V. R. Tetrahedron Lett. 1996, 37, 6615.
19. Yadav, J. S.; Shekharam, T.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1990, 843. Yadav, J. S.; Srinivas, D.; Shekharam, T. Tetrahedron Lett. 1994, 35, 3625. See also, RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986. Gurjar, M. K.; Henri, J. T., Jr.; Bose, D. S.; Rao, A. V. R. Tetrahedron Lett. 1996, 37, 6615.
20. Yadav, J. S.; Shekharam, T.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1990, 843. Yadav, J. S.; Srinivas, D.; Shekharam, T. Tetrahedron Lett. 1994, 35, 3625. See also, RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986. Gurjar, M. K.; Henri, J. T., Jr.; Bose, D. S.; Rao, A. V. R. Tetrahedron Lett. 1996, 37, 6615.
21. Yadav, J. S.; Shekharam, T.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1990, 843. Yadav, J. S.; Srinivas, D.; Shekharam, T. Tetrahedron Lett. 1994, 35, 3625. See also, RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986. Gurjar, M. K.; Henri, J. T., Jr.; Bose, D. S.; Rao, A. V. R. Tetrahedron Lett. 1996, 37, 6615.
22. a) Balmer, E.; Germain, A.; Jackson, W. P.; Lygo, B. J. Chem. Soc., Perkin Trans. 1, 1993, 399.
23. b) Nishigaichi, Y.; Kuramoto, H.; Takuwa, A. Tetrahedron Lett. 1995, 36, 3353.
24. Sarandeses, L. A.; Mourino, A.; Luche, J.-L. J. Chem. Soc., Chem. Commun. 1991, 818.
25. Rao, A. V. R.; Reddy, E. R.; Joshi, B. V.; Yadav, J. S. Tetrahedron Lett. 1987, 28, 6497.
26. a) Williams, D. R.; Jass, P. A.; Tse, H.-L. A.; Gaston, R. D. J. Am. Chem. Soc. 1990, 112, 4552.
27. b) Marshall, J. A.; Garofalo, A. W. J. Org. Chem. 1993, 58, 3675.
28. c) Marshall, J. A.; Sedrani, R. J. Org. Chem. 1991, 56, 5496.
29. d) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1, 1996, 823.
30. Hayashi, N.; Mine, T.; Fujiwara, K.; Murai, A. Chem. Lett. 1994, 2143.
31. Hasegawa, E.; Takahashi, M.; Horaguchi, T. Tetrahedron Lett. 1995, 36, 5215. Dorta, R. L.; Rodríguez, M. S.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1997, 38, 4675.
32. Hasegawa, E.; Takahashi, M.; Horaguchi, T. Tetrahedron Lett. 1995, 36, 5215. Dorta, R. L.; Rodríguez, M. S.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1997, 38, 4675.
33. Fujii, N.; Habashita, H.; Akaji, M.; Nakai, K.; Ibuka, T.; Fujiwara, M.; Tamamura, H.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1, 1996, 865.
34. a) White, J. D.; Somers, T. C.; Reddy, G. N. J. Am. Chem. Soc. 1986, 108, 5352.
35. b) White, J. D.; Somers, T. C.; Reddy, G. N. J. Org. Chem. 1992, 57, 4991.
36. c) White, J. D.; Reddy, G. N.; Spessard, G. O. J. Chem. Soc., Perkin Trans. 1, 1993, 759.
37. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
38. Details will be reported elsewhere.