The use of chiral diferrocenyl diselenidcs for highly selective asymmetric intramolecular selenocyclisation

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1999, Pages 1511-1516

  Takada, Hiroya ^a   Nishibayashi, Yoshiaki ^a   Uemura, Sakac ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001278386     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901087d     Document Type: Article

References (48)

1. For example, (a) Organoseleiiiinn Chemistry, ed. D. Liotta, Wiley, New York, 1987, p. 127;
2. (b) C. Paulmier, Selenium Reagents and Intermediates in Organic Synthesis, Pergamon Press, Oxford, 1986;
3. The chemistry of organic selenium and tellurium compounds, vol. 1, ed. S. Patai and Z. Rappoport and vol. 2, ed. S. Patai, Wiley, New York, 1986 and 1987.
4. K. Hiroi and S. Sato, Synthesis, 1985, 635.
5. C. Paulmier, F. Outurquin and J.-C. Plaquevent, Tetrahedron Lett., 1988, 29, 5889.
6. (a) S. Tomoda, K. Fujita and M. Iwaoka, Phosphorus Sulfur Silicon Relat. Elem., 1992, 67, 247;
7. (b) S. Tomoda, K. Fujita and M. Iwaoka, Chem. Lett., 1992, 1123;
8. S. Tomoda, K. Fujita and M. Iwaoka, J. Chem. Soc., Chem. Commun., 1990, 129;
9. S. Tomoda and M. Iwaoka, Chem. Lett., 1988, 1895.
10. H. J. Reich and K. E. Yelm, J. Org. Chem., 1991, 56, 5672.
11. (a) R. Déziel, E. ' Malenfant, C. Thibault, S. Fréchette and M. Gravel, Tetrahedron Lett., 1997, 38, 4753;
12. (b) R. Déziel and E. Malenfant, J. Org. Chem., 1996, 61, 1875;
13. R. Déziel and E. Malenfant, J. Org. Chem., 1995, 60, 4660;
14. R. Déziel, S. Goulet, L. Grenie, J. Bordelean and J. Dernier, J. Org. Chem., 1993, 58, 3619.
15. (a) K. Fujita, K. Murata, M. Iwaoka and S. Tomoda, Tetrahedron, 1997. 53, 2029;
16. (b) K. Fujita, K. Murata, M. Iwaoka and S. Tomoda, Tetrahedron Lett., 1995, 36, 5219;
17. K. Fujita, K. Murata, M. Iwaoka and S. Tomoda, J. Chem. Soc., Chem. Commun., 1995, 1641;
18. K. Fujita, M. Iwaoka and S. Tomoda, Chem. Lett., 1994, 923.
19. (a) T. G. Back and B. P. Dyck, Chem. Commun., 1996, 2527;
20. (b) T. G. Back, B. P. Dyck and M. Parvez, J. Org. Chem., 1995, 60, 703.
21. (a) G. Fragale, M. Neuburgerand T. Wirth, Chem. Commun., 1998, 1867;
22. (b) T. Wirth, G. Fragale and M. Spichty, J. Am. Chem. Soc., 1998. 120, 3376;
23. T. Wirth, Liebigs Ann.lRecl, 1997, 2189 and references cited therein;
24. T. Wirth, Angew. Chem., Int. Ed. Engi, 1995, 34, 1726.
25. (a) S. Fukuzawa, Y. Kasugahara and S. Uemura, Tetrahedron Lett., 1994, 35, 9403;
26. (b) S. Fukuzawa, K. Takahashi, H. Kalo and H. Yamazaki, J. Org. Chem, 1997, 62, 7711.
27. M. Tiecco, L. Testaferri, C. Santi, F. Marini, L. Bagnoli and A. Temperini, Tetrahedron Lett., 1998, 39, 2809.
28. Y. Nishibayashi, S. K. Srivastava, H. Takada, S. Fukuzawa and S. Uemura, J. Chem. Soc., Chem. Commun., 1995, 2321.
29. (a) Y. Nishibayashi, J. D. Singh, S. Fukuzawa and S. Uemura, J. Org. Chem., 1995, 60, 4114;
30. (b) Y. Nishibayashi, J. D. Singh, S. Uemura and S. Fukuzawa, Tetrahedron Lett., 1994, 35, 3115.
31. (a) Y. Nishibayashi and S. Uemura, Rev. Heteroatom. Chem., 1996, 14, 83;
32. (b) Y. Nishibayashi, J. D. Singh, Y. Arikawa, S. Uemura and M. Hidai, J. Organometal. Chem., 1997, 531, 13;
33. Y. Nishibayashi, K. Segawa, J. D. Singh, S. Fukuzawa, K. Ohe and S. Uemura, Organometallics, 1996, 15, 370;
34. Y. Nishibayashi, J. D. Singh, K. Segawa, S. Fukuzawa and S. Uemura, J. Chem. Soc., Chem. Commun., 1994, 1375.
35. G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar and R. J. Butcher, Chem. Commun., 1998, 2227. '
36. For review, see for example: K. E. Harding and T. H. Tiner, Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 4, ch. 1.9.
37. (a) D. L. J. Clive, G. Chittattu, N. J. Curtis, W. A. Kiel and C. K. Wong, J. Chem. Soc., Çhem. Commun., 1977, 725;
38. (b) D. L. J. Clive, C. G. Russell, G. Chittattu and A. Singh, Tetrahedron, 1980, 36, 1399;
39. D. L. J. Clive, G. Chittattu, V. Farina, A. Singh, C. K. Wong, W. A. Kiel and S. M. Menchen, J. Org. Chem., 1980, 45, 2120;
40. K. C. Nicolaou and Z. Lysenko, Tetrahedron Lett., 1977, 1257;
41. (e) K. C. Nicolaou, Tetrahedron, 1981, 37, 4097.
42. Hefe R of (R, S) shows the absolute configuration at the carbon of the l-(dimethylamino)ethyl moiety, while S of (R, S) shows the configuration around the ferrocene axis.
43. (a) T. Hafner and H. U. Reibig, Liebigs Ann. Chem. 1989, 937;
44. (b) K. Mori, Tetrahedron, 1975, 31, 3011.
45. G. Gokei and I. Ugi, J. Chem. Educ., 1972, 49, 82.
46. R. G. Salomon and S. Ghosh, Org. Synlh., 1984, 62, 125.
47. M. R. Gagné, C. L. Stern and T. J. Marks, J. Am. Chem. Soc., 1992, 114, 275.
48. K. Maruyama, T. Ogawa, Y. Kubo and T. Araki, J. Chem. Soc., Perkin Trans. I, 1985, 2025.