A study of asymmetric protonation with chiral β-hydroxy sulfoxides. Asymmetric synthesis of (-)-epibatidine

Chemical Communications

Volumn , Issue 19, 1997, Pages 1857-1858

  Kosugi, Hiroshi ^a   Abe, Makito ^a   Hatsuda, Ryota ^a   Uda, Hisashi ^a   Kato, Michiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002636545     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704779g     Document Type: Article

References (30)

1. T. F. Spande, H. M. Garraffo, M. W. Edwards, H. J. C. Yeh, L. Pannell and J. W. Daly, J. Am. Chem. Soc., 1992, 114, 3475.
2. (a) C. A. Broka, Tetrahedron Lett., 1993, 34, 3251;
3. (b) D. F. Huang and T. Y. Shen, Tetrahedron Lett., 1993, 34, 4477;
4. (c) S. R. Fletcher, R. Baker, M. S. Chambers, S. C. Hobbs and P. J. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 1216;
5. (d) S. C. Clayton and A. C. Regan, Tetrahedron Lett., 1993, 34, 7493;
6. (e) E. J. Corey, T.-P. Loh, S. AchyuthaRao, D. C. Daley and S. Sarshar, J. Org. Chem., 1993, 58, 5600;
7. (f) S. R. Fletcher, R. Baker, M. S. Chambers, R. H. Herbert, S. C. Hobbs, S. R. Thomas, H. M. Verrier, A. P. Watt and R. B. Ball, J. Org. Chem., 1994, 59, 1771;
8. (g) C. Stzántay, Z. Kardos-Balogh, I. Moldvai, C. Stzántay, Jr., E. Majar-Temesváry and G. Blaskó, Tetrahedron Lett., 1994, 35, 3171;
9. (h) K. Senokuchi, H. Nakai, M. Kawamura, N. Katsube, S. Nonaka, H. Sawaragi and N. Hamanaka, Synlett, 1994, 343;
10. (i) K. Sestanj, E. Melenski and L. Jirkovsky, Tetrahedron Lett., 1994, 35, 5417;
11. (j) S. Y. Ko, J. Lerpiniere, I. D. Linney and R. Wrigglesworth, J. Chem. Soc., Chem. Commun., 1994, 1775;
12. (k) E. Albertini, A. Barco, S. Benetti, C. D. Risi, G. P. Pollini, R. Romagnoli and V. Zanirato, Tetrahedron Lett., 1994, 35, 9297;
13. (l) P. L. Koitan and F. I. Carroll, Synth. Commun., 1995, 25, 63;
14. (m) R. Xu. G. Chu and D. Bai, Tetrahedron Lett., 1996, 37, 1463;
15. (n) C. Zhang and M. L. Trudell, J. Org. Chem., 1996, 61, 7189.
16. Asymmetrie synthesis: B. M. Trost and G. R. Cook, Tetrahedron Lett., 1996, 37, 7485.
17. H. Kosugi, K. Hoshino and H. Uda, presented in part at the 16th International Symposium on the Organic Chemistry of Sulfur (ISOCS), Merseburg, 1994; the abstract appeared in the Proceedings, which have been published: Phosphorus Sulfur Silicon, 1994, 95-96, 401; H. Kosugi, K. Hoshino and H. Uda, Tetrahedron Lett., in the press.
18. H. Kosugi, K. Hoshino and H. Uda, presented in part at the 16th International Symposium on the Organic Chemistry of Sulfur (ISOCS), Merseburg, 1994; the abstract appeared in the Proceedings, which have been published: Phosphorus Sulfur Silicon, 1994, 95-96, 401; H. Kosugi, K. Hoshino and H. Uda, Tetrahedron Lett., in the press.
19. H. Kosugi, K. Hoshino and H. Uda, presented in part at the 16th International Symposium on the Organic Chemistry of Sulfur (ISOCS), Merseburg, 1994; the abstract appeared in the Proceedings, which have been published: Phosphorus Sulfur Silicon, 1994, 95-96, 401; H. Kosugi, K. Hoshino and H. Uda, Tetrahedron Lett., in the press.
20. R. K. Boeckman and M. Ramaiah, J. Orig. Chem., 1977, 42, 1581.
21. F. Bravo, E. Piovosi and G. Resnati, Synthesis, 1986, 579; T. Yamazaki, N. Ishikawa, H. Iwatsubo and T. Kitazume, J. Chem. Soc., Chem. Commun., 1987, 1340; P. Bravo, M. Frigerio and G. Resnati, Synthesis, 1988, 955.
22. F. Bravo, E. Piovosi and G. Resnati, Synthesis, 1986, 579; T. Yamazaki, N. Ishikawa, H. Iwatsubo and T. Kitazume, J. Chem. Soc., Chem. Commun., 1987, 1340; P. Bravo, M. Frigerio and G. Resnati, Synthesis, 1988, 955.
23. F. Bravo, E. Piovosi and G. Resnati, Synthesis, 1986, 579; T. Yamazaki, N. Ishikawa, H. Iwatsubo and T. Kitazume, J. Chem. Soc., Chem. Commun., 1987, 1340; P. Bravo, M. Frigerio and G. Resnati, Synthesis, 1988, 955.
24. N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, 1983.
25. K. C. Cundy and P. A. Crooks, J. Chromatogr., 1983, 281, 17; R. Charles and E. Gil-Av, J. Chromatogr., 1984, 298, 516; A. Dobashi, Y. Motoyama, K. Kinoshita, S. Hara and N. Fukusaku, Anal. Chem., 1987, 59, 2209; W. L. Tsai, K. Hermann, E. Hug, B. Rhode and A. S. Dreiding, Helv. Chim. Acta. 1985, 68, 2238; R. Matusch and C. Coors, Angew. Chem., Int. Ed. Engl., 1989, 28, 626; P. Diter, S. Taudien, O. Samuel and H. B. Kagan, J. Org. Chem., 1994, 59, 370.
26. K. C. Cundy and P. A. Crooks, J. Chromatogr., 1983, 281, 17; R. Charles and E. Gil-Av, J. Chromatogr., 1984, 298, 516; A. Dobashi, Y. Motoyama, K. Kinoshita, S. Hara and N. Fukusaku, Anal. Chem., 1987, 59, 2209; W. L. Tsai, K. Hermann, E. Hug, B. Rhode and A. S. Dreiding, Helv. Chim. Acta. 1985, 68, 2238; R. Matusch and C. Coors, Angew. Chem., Int. Ed. Engl., 1989, 28, 626; P. Diter, S. Taudien, O. Samuel and H. B. Kagan, J. Org. Chem., 1994, 59, 370.
27. K. C. Cundy and P. A. Crooks, J. Chromatogr., 1983, 281, 17; R. Charles and E. Gil-Av, J. Chromatogr., 1984, 298, 516; A. Dobashi, Y. Motoyama, K. Kinoshita, S. Hara and N. Fukusaku, Anal. Chem., 1987, 59, 2209; W. L. Tsai, K. Hermann, E. Hug, B. Rhode and A. S. Dreiding, Helv. Chim. Acta. 1985, 68, 2238; R. Matusch and C. Coors, Angew. Chem., Int. Ed. Engl., 1989, 28, 626; P. Diter, S. Taudien, O. Samuel and H. B. Kagan, J. Org. Chem., 1994, 59, 370.
28. K. C. Cundy and P. A. Crooks, J. Chromatogr., 1983, 281, 17; R. Charles and E. Gil-Av, J. Chromatogr., 1984, 298, 516; A. Dobashi, Y. Motoyama, K. Kinoshita, S. Hara and N. Fukusaku, Anal. Chem., 1987, 59, 2209; W. L. Tsai, K. Hermann, E. Hug, B. Rhode and A. S. Dreiding, Helv. Chim. Acta. 1985, 68, 2238; R. Matusch and C. Coors, Angew. Chem., Int. Ed. Engl., 1989, 28, 626; P. Diter, S. Taudien, O. Samuel and H. B. Kagan, J. Org. Chem., 1994, 59, 370.
29. K. C. Cundy and P. A. Crooks, J. Chromatogr., 1983, 281, 17; R. Charles and E. Gil-Av, J. Chromatogr., 1984, 298, 516; A. Dobashi, Y. Motoyama, K. Kinoshita, S. Hara and N. Fukusaku, Anal. Chem., 1987, 59, 2209; W. L. Tsai, K. Hermann, E. Hug, B. Rhode and A. S. Dreiding, Helv. Chim. Acta. 1985, 68, 2238; R. Matusch and C. Coors, Angew. Chem., Int. Ed. Engl., 1989, 28, 626; P. Diter, S. Taudien, O. Samuel and H. B. Kagan, J. Org. Chem., 1994, 59, 370.
30. K. C. Cundy and P. A. Crooks, J. Chromatogr., 1983, 281, 17; R. Charles and E. Gil-Av, J. Chromatogr., 1984, 298, 516; A. Dobashi, Y. Motoyama, K. Kinoshita, S. Hara and N. Fukusaku, Anal. Chem., 1987, 59, 2209; W. L. Tsai, K. Hermann, E. Hug, B. Rhode and A. S. Dreiding, Helv. Chim. Acta. 1985, 68, 2238; R. Matusch and C. Coors, Angew. Chem., Int. Ed. Engl., 1989, 28, 626; P. Diter, S. Taudien, O. Samuel and H. B. Kagan, J. Org. Chem., 1994, 59, 370.