Allylation of imines with allyltrimethylsilane and experimental evidences for a fluoride-triggered autocatalysis mechanism of the Sakurai- Hosomi reaction

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4233-4237

  Wang, De Kun ^a   Zhou, Yong Gui ^a   Tang, Yong ^a   Hou, Xue Long ^a   Dai, Li Xin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION;

EID: 0033546242     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980767y     Document Type: Article

References (50)

1. For recent reviews, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. (b) Rough, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds. (Vol. 2 editor C. H. Heathcock); Pergamon Press: Oxford, 1991; pp 1-53.
3. (c) Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.(Vol. 2 editor C. H. Heathcock); Pergamon Press: Oxford, 1991; pp 563-593.
4. (d) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
5. (e) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
6. (a) Yasuda, M.; Fujibayashi, T.; Shibata, I.; Baba, A.; Matsuda, H.; Sonada, N. Chem. Lett. 1995, 167.
7. (b) Jephcote, V. J.; Thomas, E. J. Tetrahedron Lett. 1985, 26, 5327.
8. (c) Yamamoto, Y.; Maruyama, K.; Naruta, Y.; Yatagai, H. J. Am. Chem Soc. 1980, 102, 7101.
9. (d) Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron 1984, 40, 2239.
10. (e) Jephcote, V. J.; Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1984, 800.
11. (f) Yanngisawa, A.; Morodome, M.; Nakashima, H.; Yamamoto, H. Synlett 1997, 1309.
12. (g) Yanagisawa, A.; Inoun, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356 and references therein.
13. (a) Chen, D. L.; Li, C. J. Tetrahedron Lett. 1996, 37, 295.
14. (b) Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747.
15. (c) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
16. (d) Li, C. J. Chem. Rev. 1993, 93, 2023.
17. (e) For an excellent book, see: Li, C. J.; Chan, T. H. In Organic Reaction in Aqueous Media; John Wiley & Sons, Inc.: 1997; p 75 and references therein.
18. For some leading references, see: (a) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339. (b) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 1, 5495.
19. For some leading references, see: (a) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339. (b) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 1, 5495.
20. For some leading references, see: (a) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339. (b) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 1, 5495.
21. (d) Corey, E. J.; Huang, H. C. Tetrahedron Lett. 1989, 30, 5235 and references therein.
22. For reviews, see: (a) Furin, G. G.; Vyazankina, O. A.; Gostevsky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675. (b) Sakurai, H. Pure Appl. Chem. 1985, 57, 1759. (c) Sakurai, H. Pure Appl. Chem. 1982, 54, 1. (d) Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
23. For reviews, see: (a) Furin, G. G.; Vyazankina, O. A.; Gostevsky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675. (b) Sakurai, H. Pure Appl. Chem. 1985, 57, 1759. (c) Sakurai, H. Pure Appl. Chem. 1982, 54, 1. (d) Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
24. For reviews, see: (a) Furin, G. G.; Vyazankina, O. A.; Gostevsky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675. (b) Sakurai, H. Pure Appl. Chem. 1985, 57, 1759. (c) Sakurai, H. Pure Appl. Chem. 1982, 54, 1. (d) Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
25. For reviews, see: (a) Furin, G. G.; Vyazankina, O. A.; Gostevsky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675. (b) Sakurai, H. Pure Appl. Chem. 1985, 57, 1759. (c) Sakurai, H. Pure Appl. Chem. 1982, 54, 1. (d) Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
26. (a) Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 19, 3043.
27. (b) Sarker, T. K.; Andersen, N. H. Tetrahedron Lett. 1978, 19, 3513.
28. (c) Deleris, G.; Dunogues, J., Calas, R.; Pisciotti, F. J. Organomet. Chem. 1974, 69, C 15.
29. (d) Deleris, G.; Dunogues, J.; Calas, R.; Pisciotti, F. J. Organomet. Chem. 1975, 93, 43.
30. (e) Able, E. W.; Rowley, R. J. J. Organomet. Chem. 1975, 84, 199.
31. (f) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 1295. (g) Generally, the Lewis acid-catalyzed allylation of carbonyl compound with allyl silane is known as the Sakurai-Hosomi reaction (Majetich suggested to name this reaction as Hosomi reaction, see ref 16a); here we further extended the name of this reaction to include the fluoride-triggered reaction.
32. (a) Kira, M.; Hino, T.; Sakurai, H. Chem. Lett. 1991, 277. They suggested that the pentacoordinate allylsilicate complexes might be involved when the following molar ratio of reagents was used: crotyltrifluorosilane/aldimine/CSF = 2/1/3-4. (b) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901.
33. (a) Kira, M.; Hino, T.; Sakurai, H. Chem. Lett. 1991, 277. They suggested that the pentacoordinate allylsilicate complexes might be involved when the following molar ratio of reagents was used: crotyltrifluorosilane/aldimine/CSF = 2/1/3-4. (b) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901.
34. (a) For a recent book, see: Majetich, G. In Organic Synthesis Theory and Application; Hudlicky, T., Ed.; JAI Press Ltd.: 1989; Vol. 1, p 173.
35. (b) Bottom, A.; Costa, A. L.; Tommaso, D. D.; Rossi, I.; Tagliavini, E. J. Am. Chem. Soc. 1997, 119, 12131.
36. Sakurai, H.; Hosomi, A.; Saito, M.; Sasaki, K.; Iguck, H.; Sasata, J.; Araki, Y. Tetrahedron 1983, 39, 883.
37. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: New York, 1960; Chapter 3.
38. For the fluoride-catalyzed Aldol reaction of enol silyl ethers with aldehydes, see: (a) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. (b) Nakmura, E.; Shimizu, M.; Kuwajima, I.; Sakata, J.; Yokoyama, K.; Noyori, R. J. Org. Chem. 1983, 48, 932.
39. For the fluoride-catalyzed Aldol reaction of enol silyl ethers with aldehydes, see: (a) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. (b) Nakmura, E.; Shimizu, M.; Kuwajima, I.; Sakata, J.; Yokoyama, K.; Noyori, R. J. Org. Chem. 1983, 48, 932.
40. DiGiorgio, P. A.; Strong, W. A.; Sommer, L. H.; Whitmore, F. C. J. Am. Chem. Soc. 1946, 68, 1380.
41. For an example of an alkoxide-induced reaction between an imine and a benzylsilane derivative, see: Shimizu, S.; Ogata, M. Synth. Commun. 1989, 19, 2219.
42. For an excellent review on reactivity of pentacoordinate silicon compounds, see: Chuit, C. C.; Corriu, R. J.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371 and references therein.
43. Love, B. E.; Raje, P. S.; Williams, T. C., II. Synlett 1994, 493.
44. (a) Campbell, K. N.; Sommers, A. H.; Campbell, B. K. J. Am. Chem. Soc. 1944, 66, 822.
45. (b) Castello, J. A.; Goldmacher, J. E.; Barton, L. A.; Kane, J. S. J. Org. Chem. 1968, 33, 3501.
46. Slutsky, J.; Kwart, H. J. Am. Chem. Soc. 1973, 95, 8684.
47. Sakurai, H. Synlett 1989, 1.
48. (a) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187.
49. (b) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649.
50. (c) Bhuyan, P. J.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1993, 34, 7975.