Silylcupration of 1,3-dienes followed by an electrophilic trapping reaction

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1861-1864

  Liepins, Vilnis ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 18044403052     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015910f     Document Type: Article

References (51)

1. (a) Fleming, I.; Roessler, F. J. Chem. Soc., Chem. Commun. 1980, 276.
2. (b) Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans. 1 1981, 2527.
3. (c) Fleming, I.; Martinez de Marigorta, E. J. Chem. Soc., Perkin Trans. 1 1999, 889.
4. (d) Barbero, A.; Pulido, F. J. Recent Res. Dev. Synth. Org. Chem. 1999, 2, 1.
5. (a) Fleming, I.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1986, 1010.
6. (b) Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. Tetrahedron Lett. 1988, 29, 1825.
7. (c) Cuadrado, P.; Gonzalez-Nogal, A. M.; Pulido, F. J.; Fleming, I.; Rowley, M. Tetrahedron 1989, 45, 413.
8. (d) Barbero, A.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1991, 2811.
9. (e) Fleming, I.; Landais, Y.; Raithby, P. R. J. Chem. Soc., Perkin Trans. 1 1991, 715.
10. (a) Fugami, K.; Nakatsukasa, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett. 1986, 6, 869.
11. (b) Fugami, K.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron Lett. 1986, 27, 2161.
12. (c) Fugami, K.; Hibino, J.; Nakatsukasa, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1988, 44, 4277.
13. Hayashi, T.; Kobayashi, T.; Kawamoto, A. M.; Yamashita, H.; Tanaka, M. Organometallics 1990, 9, 280.
14. (a) Tamao, K.; Okazaki, S.; Kumada, M. J. Organomet. Chem. 1978, J46, 87.
15. (b) Matsumoto, H.; Shono, K.; Wada, A.; Matsubara, I.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1980, 199, 185.
16. (c) Sakurai, H.; Eriyama, Y.; Kamiyama, Y.; Nakadaira, Y. J. Organomet. Chem. 1984, 264, 229.
17. (d) Carlson, C. W.; West, R. Organometallics 1983, 2, 1801.
18. Liepins, V.; Bäckvall, J.-E. Chern. Commun. 2001, 265.
19. (a) Fleming, I. In Organocopper Reagents. A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; Chapter 12, p 257.
20. (b) Fleming, I.; Roberts, R. S.; Smith, S. C. J. Chem. Soc., Perkin Trans. 1 1998, 1209.
21. (a) Blanco, F. J.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. Tetrahedron Lett. 1994, 35, 8881.
22. (b) Barbero, A.; Garcia, C.; Pulido, F. J. Tetrahedron Lett. 1999, 40, 6649.
23. (c) Barbero, A.; Garcia, C.; Pulido, F. J. Tetrahedron 2000, 56, 2739.
24. Liepins, V.; Karlström, A. S. E.; Bäckvall, J. E. Org. Lett. 2000, 2, 1237.
25. (a) Yamamoto, H.; Nomura, N.; Yanagisawa, A. Tetrahedron 1994, 50, 6017.
26. (b) Knochel, P.; Jubert, C.; Tucker, E. C.; Nowotny, S. J. Org. Chem. 1995, 60, 2762.
27. Allylic phosphates have previously been used as electrophiles in a copper-catalysed cross-coupling reaction with Grignard reagents: (a) Yanagisawa, A.; Noritake, Y.; Nomura, N.; Yamamoto, H. Synlett 1991, 251.
28. (b) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1993, 689.
29. (c) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017.
30. 3 75.4 MHz): δ 146.4, 139.3, 133.8, 133.6, 129.0, 127.8, 120.0, 109.6, 36.0, 30.2, 23.5, 22.7, 17.6, -3.0.
31. Nakamura, E.; Mori, S. Angew. Chem., Int. Ed. 2000, 39, 3750 and references therein.
32. (a) Woodward, S. Chem. Soc. Rev. 2000, 29, 393.
33. (b) Kingsbury, C. L.; Smith, R. A. J. J. Org. Chem. 1997, 62, 4629.
34. (c) Uerdingen, M.; Krause, N. Tetrahedron 2000, 56, 2799.
35. (d) Dorigo, A, E.; Wanner, J.; Schleyer, P. von R. Angew. Chem., Int. Ed. Engl. 1995, 34, 476.
36. (e) Nakamura, E.; Yamanaka, M. J. Am. Chem. Soc. 1999, 121, 8941.
37. (f) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 8273.
38. (g) Nakamura, E.; Yamanaka, M.; Mori, S. J. Am. Chem. Soc. 2000, 122, 1826.
39. (a) Posner, G. H. Org. React. 1975, 22, 253.
40. (b) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
41. (c) Bäckvall, J. E.; Sellen, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615.
42. (d) Magid, R. M. Tetrahedron 1980, 36, 1901.
43. (e) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422.
44. (f) Underiner, T.; Goering, H. L. J. Org. Chem. 1991, 56, 2563 and preceding papers in this series.
45. (g) Bäckvall, J. E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1994, 59, 4126.
46. (h) Persson, E. S. M.; Bäckvall, J. E. Acta Chem. Scand. 1995, 49, 899.
47. (i) Persson, E. S. M.; van Klaveren, M.; Grove, D. M.; Bäckvall, J. E.; van Koten, G. Chem. Eur. J. 1995, 1, 351.
48. (j) Karlström, A. S. E.; Bäckvall, J. E. Chem. Eur. J. 2001, 7, 1981.
49. (a) Miller, J. A.; Wood, H. C. S. Angew. Chem. 1964, 76, 301.
50. (b) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 1365.
51. McCallum, J. S.; Liebeskind, L. S. Synthesis 1993, 819.