Iron(III) chloride-catalyzed effective allylation reactions of aldehydes with allyltrimethylsilane

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8959-8962

  Watahiki, Tsutomu ^a   Oriyama, Takeshi ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; IRON COMPLEX; LEWIS ACID; SILANE DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; ROOM TEMPERATURE; STEREOSPECIFICITY;

EID: 0037010804     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02107-X     Document Type: Article

References (47)

1. For leading review, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293; (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
2. For leading review, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293; (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
3. For leading review, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293; (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
4. For leading review, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293; (c) Marshall, J. A. Chem. Rev. 1996, 96, 31. (d) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
5. (a) Hollis T.K., Robinson N.P., Whelan J., Bosnich B. Tetrahedron Lett. 34:1993;4309;
6. (b) Maeta H., Nagasawa T., Handa Y., Takei T., Osamura Y., Suzuki K. Tetrahedron Lett. 36:1995;899;
7. (c) Gauthier, D. R.; Carreira, E. M. Angew. Chem. 1996, 108, 2521;
8. Angew. Chem. Int. Ed. Engl. 1996, 35, 2363;
9. (d) Kaur G., Manju K., Trehan S. Chem. Commun. 1996;581;
10. (e) Komatsu N., Uda M., Suzuki H. Tetrahedron Lett. 38:1997;7215;
11. (f) Marx A., Yamamoto H. Angew. Chem. Int. Ed. 39:2000;178;
12. (g) Yasuda M., Onishi Y., Ito T., Baba A. Tetrahedron Lett. 41:2000;2425;
13. (h) Yadav J.S., Chand P.K., Anjaneyulu S. Tetrahedron Lett. 43:2002;3783;
14. Hosomi A., Sakurai H. Tetrahedron Lett. 1976;1295.
15. Hayashi T., Kabeta K., Hamachi I., Kumada M. Tetrahedron Lett. 24:1983;2865.
16. Denmark S.E., Henke B.R., Weber E.J. J. Am. Chem. Soc. 109:1987;2512.
17. Nishigaichi Y., Takuwa A., Jodai A. Tetrahedron Lett. 32:1991;2383.
18. Yanagisawa A., Morodome M., Nakashima H., Yamamoto H. Synlett. 1997;1309.
19. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
20. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
21. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
22. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
23. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
24. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
25. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
26. Allylation of aldehydes with allylsilanes: (a) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745; (b) Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651; (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822. With allylstannanes: (d) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958; (e) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639; (f) Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283; (g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 319. With allylgermane: (h) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
27. Iranpoor N., Salehi P. Synthesis. 1994;1152.
28. Christoffers J. J. Chem. Soc., Perkin Trans. 1. 1997;3141.
29. Barton D.H.R., Hill D.R., Hu B. Tetrahedron Lett. 38:1997;1711.
30. Salehi P., Iranpoor N., Behbahani F.K. Tetrahedron. 54:1998;943.
31. Sen S.E., Roach S.L., Smith S.M., Zhang Y.Z. Tetrahedron Lett. 39:1998;3969.
32. Sharma G.V.M., Mahalingam A.K., Nagarajan M., Ilangovan A., Radhakrishna P. Synlett. 1999;1200.
33. Barrett I.C., Langille J.D., Kerr M.A. J. Org. Chem. 65:2000;6268.
34. Chibiryaev A.M., Kimpe N.D., Tkachev A.V. Tetrahedron Lett. 41:2000;8011.
35. Yus M., Pastor I.M., Gomis J. Tetrahedron. 57:2001;5799.
36. Sharma G.V.M., Kumar K.R., Sreenivas P., Krishna P.R., Chorghade M.S. Tetrahedron: Asymmetry. 13:2002;687.
37. Vidari G., Beszant S., Merabet J.E., Bovolenta M., Zanoni G. Tetrahedron Lett. 43:2002;2687.
38. 3: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta. 1983, 66, 1655; (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053; (c) Kang, K.-T.; Kim, S. S.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 3495; (d) Kuroda, C.; Koshio, H.; Koito, A.; Sumiya, H.; Murase, A.; Hirono, Y. Tetrahedron 2000, 56, 6441.
39. 3: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta. 1983, 66, 1655; (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053; (c) Kang, K.-T.; Kim, S. S.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 3495; (d) Kuroda, C.; Koshio, H.; Koito, A.; Sumiya, H.; Murase, A.; Hirono, Y. Tetrahedron 2000, 56, 6441.
40. 3: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta. 1983, 66, 1655; (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053; (c) Kang, K.-T.; Kim, S. S.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 3495; (d) Kuroda, C.; Koshio, H.; Koito, A.; Sumiya, H.; Murase, A.; Hirono, Y. Tetrahedron 2000, 56, 6441.
41. 3: (a) Denmark, S. E.; Weber, E. J. Helv. Chim. Acta. 1983, 66, 1655; (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053; (c) Kang, K.-T.; Kim, S. S.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 3495; (d) Kuroda, C.; Koshio, H.; Koito, A.; Sumiya, H.; Murase, A.; Hirono, Y. Tetrahedron 2000, 56, 6441.
42. 3 was purchased from Aldrich Company.
43. Ishii A., Kotera O., Saeki T., Mikami K. Synlett. 1997;1145.
44. Fang X., Watkin J.G., Warner B.P. Tetrahedron Lett. 41:2000;447.
45. 1H NMR and IR spectra.
46. Heathcock C.H., Kiyooka S., Blumenkopf T.A. J. Org. Chem. 49:1984;4214.
47. Davis A.P., Jaspars M. J. Chem. Soc., Perkin Trans. 1. 1992;2111.