Bismuth bromide as an efficient and versatile catalyst for the cyanation and allylation of carbonyl compounds and acetals with organosilicon reagents

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7215-7218

  Komatsu, Naoki ^a   Uda, Masato ^a   Suzuki, Hitomi ^a   Takahashi, Toshikazu ^b   Domae, Terutomo ^b   Wada, Makoto ^b  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ETHER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030698837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01719-X     Document Type: Article

References (46)

1. Part of this work was presented at the 6th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-6), Kyoto, in November 1994 and the 1995 International Chemical Congress of Pacific Basin Societies (PACIFICHEM '95), Honolulu, Hawaii, in December 1995.
2. For reviews see; (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249.;
3. (b) Postel, M.; Dunach, E. Coordination Chem. Rev. 1996, 155, 127.;
4. (c) Suzuki, H. Farumashia 1996, 32, 1501.;
5. (d) Wada, M.; Ohki, H. J. Synth. Org. Chem. Jpn. 1989, 47, 425.
6. (a) Boisselier, V. L.; Postel, M.; Duñach, E. Chem. Commun. 1997, 95.;
7. (b) Boisselier, V. L.; Postel, M.; Duñach, E. Tetrahedron Lett. 1997, 38, 2981.;
8. (c) Montero, J.-L.; Winum, J.-Y.; Leydet, A.; Kamel, M.; Pavia, A. A.; Roque, J.-P. Carbohydr. Res. 1997, 297, 175.;
9. (d) Roux, C. L.; Dubac, J. Organomet. 1996, 15, 4646.;
10. (e) Roux, C. L.; Mandrou, S.; Dubac, J. J. Org. Chem. 1996, 61, 3885.;
11. (f) Boisselier, V. L.; Coin, C.; Postel, M.; Duñach, E. Tetrahedron 1995, 51, 4991.;
12. (g) Boisselier, V. L.; Dunach, E.; Postel, M. J. Organomet. Chem. 1994, 482, 119.
13. (h) Roux, C. L.; G-Iloughmane, H.; Dubac, J. J. Org. Chem. 1994, 59, 2238.;
14. (i) Labrouillére, M.; Roux, C. L.; G-Iloughmane, H.; Dubac, J. Synlett 1994, 723.;
15. (j) Zevaco, T.; Duñach, E.; Postel, M. Tetrahedron Lett. 1993, 34, 2601.
16. (k) Roux, C. L.; G-Iloughmane, H.; Dubac, J. J. Org. Chem. 1993, 55, 1835.;
17. (l) Roux, C. L.; G-Iloughmane, H.; Dubac, J. Bull. Soc. Chim. Fr. 1993, 130, 832.
18. (a) Komatsu, N; Taniguchi, A.; Uda, M; Suzuki, H. J. Chem. Soc., Chem. Commun. 1996, 1847.;
19. (b) Komatsu, N; Uda, M; Suzuki, H. Synlett 1995, 984.;
20. (c) Wada, M.; Takeichi, E.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1991, 64, 990.;
21. (d) Ohki, H.; Wada, M.; Akiba, K.-Y. Tetrahedron Lett. 1988, 29, 4719.;
22. (e)Wada, M.; Ohki, H.; Akiba, K.-Y. J. Chem. Soc., Chem. Commun. 1987, 708.
23. (a) For review see; Groutas, W. C.; Felker, D. Synthesis 1980, 861.;
24. (b) Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 2525 and references cited therein.
25. For reviews see; (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207;
26. (b) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. (N. Y.) 1989, 37, 57.;
27. (c) Hosomi, A. Acc. Chem. Res. 1988, 21, 200.;
28. (d) Schinzer, D. Synthesis 1988, 263.
29. Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.
30. 3 is recommended to be stored in a desiccator to avoid humidity.
31. When the reagents contain an impurity such as carboxylic acid, 2 equiv of aldehyde often reacts with allyltrimethylsilane to afford pyran derivatives, reducing the yield of the desired product considerably; see: (a) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.;
32. (b) Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973;
33. (c) Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441.
34. Roux, C. L.; Maraval, M.; Borredon, M. E.; G-Iloughmane, H.; Dubac, J.Tetrahedron Lett. 1992,33,1053.
35. Gandini, A. Adv. Polm. Sci. 1977, 25, 47.
36. Denmark, S. E.; Henke, B. R.; Weber, E. J. Am. Chem. Soc. 1987, 109, 2512.
37. Allylation of aldehydes using allyltrichlorosilanes in DMF in the absence of a catalyst was recently reported; see, Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620
38. (a) Davis, A. P.; Jaspars, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 470.;
39. (b) Davis, A. P.; Jaspars, M. J. Chem. Soc., Perkin. Trans. I 1992, 2111.
40. Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176.
41. Triryl perchlorate does not catalyze the allylation of benzaldehyde with allyltrimethylsilane; Mukaiyama, T.; Nagaoka, H.; Murakami, M.; Ohshima, M. Chem. Lett. 1985, 977.
42. Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745.
43. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71.
44. Sakurai, H.; Sasaki, K.; Hosomi, A. Tetrahedron Lett. 1981, 22, 745.
45. Glaudemans, C. P. J.; Fletcher, Jr., H. G. Methods Carbohydr. Chem. 1972, 6, 373.
46. Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383.