Allylsilylation of Carbon-Carbon and Carbon-Oxygen Unsaturated Bonds via a Radical Process

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5740-5741

  Miura, Katsukiyo ^a   Saito, Hiroshi ^a   Nakagawa, Takahiro ^a   Hondo, Takeshi ^a   Tateiwa, Jun Ichi ^a   Sonoda, Motohiro ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001129264     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981027s     Document Type: Article

References (31)

1. Studies on Organosilicon Chemistry. 142.
2. For reviews see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333. (d) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159. (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
3. For reviews see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333. (d) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159. (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
4. For reviews see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333. (d) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159. (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
5. For reviews see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333. (d) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159. (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
6. For reviews see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333. (d) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159. (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
7. For reviews see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. (c) Negishi, E. Pure Appl. Chem. 1981, 53, 2333. (d) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 159. (e) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
8. (a) Miura, K; Itoh, D.; Hondo, T.; Saito, H.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1996, 37, 8539.
9. (b) Miura, K.; Matsuda, T.; Hondo, T.; Ito, H.; Hosomi, A. Synlett 1996, 555.
10. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829.
11. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
12. (a) Chatgilialoglu, C.; Ballestri, M.; Vecchi, D.; Curran, D. P. Tetrahedron Lett. 1996, 37, 6383.
13. (b) Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Curran, D. P. Tetrahedron Lett. 1996, 37, 6387.
14. For studies on chemical properties of silyl radicals see: Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229.
15. For studies on the ionic allylsilylation see: (a) Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781. (b) Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159. (c) Yeon, S. H.; Lee, B. W.; Yoo, B. R.; Suk, M.-Y.; Jung, I. N. Organometallics 1995, 14, 2361.
16. For studies on the ionic allylsilylation see: (a) Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781. (b) Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159. (c) Yeon, S. H.; Lee, B. W.; Yoo, B. R.; Suk, M.-Y.; Jung, I. N. Organometallics 1995, 14, 2361.
17. For studies on the ionic allylsilylation see: (a) Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781. (b) Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159. (c) Yeon, S. H.; Lee, B. W.; Yoo, B. R.; Suk, M.-Y.; Jung, I. N. Organometallics 1995, 14, 2361.
18. (a) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115.
19. (b) Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826.
20. (a) Bulliard, M.; Zeitz, H.-G.; Giese, B. Synlett 1991, 423 and 425.
21. (b) Giese, B.; Damm, W.; Wetterich, F.; Zeitz, H.-G. Tetrahedron Lett. 1992, 33, 1863.
22. (a) Miura, K.; Itoh, D.; Hondo, T.; Hosomi, A. Tetrahedron Lett. 1994, 35, 9605.
23. (b) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085.
24. (c) Giese, B.; González-Gómez, J. A.; Lachhein, S.; Metzger, J. O. Angew. Chem., Int. Ed. Engl. 1987, 26, 479.
25. In contrast, the reaction of 13e with 2b′ gave the allylstannylation product in 84% yield with the same regio- and stereocontrol.
26. Bogen, S.; Malacria, M. J. Am. Chem. Soc. 1996, 118, 3992 and references therein.
27. Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994.
28. Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
29. 3) to afford a homoallyl alcohol after destannylation of the crude product (unpublished result).
30. The reactivity of silyl radicals toward carbonyl compounds is well-known as described in ref 7.
31. Functionalized substrates are not used in the Lewis acid-mediated allylsilylations (ref 8).