Nickel(0)-catalyzed asymmetric cross-coupling reactions of allylic compounds with arylboronic acids

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 1, 2001, Pages 15-18

  Chung, Kang Go ^a   Miyake, Yoshihiro ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 52549083582     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. N. Miyaura and S. Suzuki, Chem. Rev., 1995, 95, 2457.
2. (a) C. S. Cho, S. Motofusa and S. Uemura, Tetrahedron Lett., 1994, 35, 1739
3. (b) C. S. Cho, S. Motofusa, K. Ohe, S. Uemura and S. C. Shim, J. Org. Chem., 1995, 60, 883
4. (c) M. Sakai, H. Hayashi and N. Miyaura, Organometallics, 1997, 16, 4229
5. (d) Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai and N. Miyaura, J. Am. Chem. Soc., 1998, 120, 5579
6. (e) Y. Takaya, M. Ogasawara and T. Hayashi, Tetrahedron Lett., 1999, 40, 6957.
7. M. Sakai, M. Ueda and N. Miyaura, Angew. Chem., Int. Ed., 1998, 37, 3279.
8. (a) J.-Y. Legros and J.-C. Fiaud, Tetrahedron Lett., 1990, 31, 7453
9. (b) B. M. Trost and M. D. Spagnol, J. Chem. Soc., Perkin Trans. 1, 1993, 1673
10. (c) Y. Kobayashi, R. Mizojiri and E. Ikeda, J. Org. Chem., 1996, 61, 5391
11. (d) Y. Uozumi, H. Danjo and T. Hayashi, J. Org. Chem., 1999, 64, 3384.
12. C. S. Cho, K. Ohe and S. Uemura, J. Organomet. Chem., 1995, 496, 221.
13. (a) C. S. Cho, K. Itotani and S. Uemura, J. Organomet. Chem., 1993, 443, 253
14. (b) C. S. Cho and S. Uemura, J. Organomet. Chem., 1994, 465, 85
15. (c) N. A. Bumagin and D. N. Korolev, Tetrahedron Lett., 1999, 40, 3057.
16. S. Y. Cho and M. Shibasaki, Tetrahedron: Asymmetry, 1998, 9, 3751.
17. B. M. Trost and D. L. V. Vranken, Chem. Rev., 1996, 96, 395.
18. Recently, Pd-catalyzed allylic alkylation using dimethyl malonate in the presence of chiral oxazolinylferrocenylphosphines was reported; K. H. Ahn, C.-W. Cho, J. Park and S. Lee, Tetrahedron: Asymmetry, 1997, 8, 1179.
19. (a) T. Hiyama and N. Wakasa, Tetrahedron Lett., 1985, 26, 3259
20. (b) A. F. Indolese and G. Consiglio, Organometallics, 1994, 13, 2230
21. (c) N. Nomura and T. V. RajanBabu, Tetrahedron Lett., 1997, 38, 1713 and references cited therein. Recently, Cu-catalyzed allylic substitution using "hard" nucleophiles was reported
22. (d ) M. van Klaveren, E. S. M. Persson, A. del Villar, D. M. Grove, J.-E. Bäckvall and G. van Koten, Tetrahedron Lett., 1995, 36, 3059
23. (e) F. Dübner and P. Knochel, Angew. Chem., Int. Ed., 1999, 38, 379.
24. T. Hayashi, M. Konishi and M. Kumada, J. Chem. Soc., Chem. Commun., 1984, 107 and references cited therein.
25. (a) Y. Nishibayashi and S. Uemura, Synlett, 1995, 79
26. (b) Y. Nishibayashi, K. Segawa, Y. Arikawa, K. Ohe and S. Uemura, J. Organomet. Chem., 1997, 545-546, 381.
27. (a) Y. Nishibayashi, K. Segawa, K. Ohe and S. Uemura, Organometallics, 1995, 14, 5486
28. (b) Y. Nishibayashi, K. Segawa, H. Takada, K. Ohe and S. Uemura, Chem. Commun., 1996, 847
29. (c) Y. Nishibayashi, I. Takei, S. Uemura and M. Hidai, Organometallics, 1998, 17, 3420
30. (d) I. Takei, Y. Nishibayashi, Y. Arikawa, S. Uemura and M. Hidai, Organometallics, 1999, 18, 2271.
31. (a) Y. Arikawa, M. Ueoka, K. Matoba, Y. Nishibayashi, M. Hidai and S. Uemura, J. Organomet. Chem., 1999, 572, 163
32. (b) Y. Nishibayashi, I. Takei, S. Uemura and M. Hidai, Organometallics, 1999, 18, 2291.
33. 2:ligand I = 1:1).
34. 3.
35. In all cases, the yield of compound 3w was below 6%.
36. There are examples in which the product having a chiral center was obtained predominantly with good enantioselectivity in the reaction using an unsymmetrical substrate and a Grignard reagent; see refs. 9a and 18.
37. G. Consiglio, O. Piccolo and L. Roncetti, Tetrahedron, 1986, 42, 2043.
38. J.-L. Luche, L. Rodrigues-Hahn and P. Crabbè, J. Chem. Soc., Chem. Commun., 1978, 601.
39. S. F. Martin and P. J. Garrison, J. Org. Chem., 1982, 47, 1513.
40. P. Von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573.
41. F. R. Bean and J. R. Johnson, J. Am. Chem. Soc., 1932, 54, 4415.
42. T. Ukai, H. Kawazura and Y. Ishii, J. Organomet. Chem., 1974, 65, 253.
43. W. J. Cherwinski, B. F. G. Johnson and J. Lewis, J. Chem. Soc., Dalton Trans., 1974, 1405.
44. G. Berti, B. Macchia, F. Macchia and L. Monti, J. Org. Chem., 1968, 33, 4045.