An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions

Journal of the American Chemical Society

Volumn 127, Issue 34, 2005, Pages 11934-11935

  Imamoto, Tsuneo ^a   Sugita, Keitaro ^a   Yoshida, Kazuhiro ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ESTER; LIGAND; METAL; METAL COMPLEX; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; PHOSPHORUS; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; ROOM TEMPERATURE;

EID: 24144436977     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053458f     Document Type: Article

References (45)

1. For representative reviews, see: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3069.
2. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110.
3. Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, pp 121-182.
4. Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1-40.
5. (e) Guiry, P. J.; Saunders, C. P. Adv. Synth. Catal. 2004, 346, 497-537.
6. For recent representative examples, see: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540.
7. (b) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890.
8. (c) Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425-3428.
9. (d) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197-1200.
10. (e) Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612-1614.
11. (f) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614.
12. (g) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348-2350.
13. (h) Tang, W.; Wang, W.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 943-946.
14. (i) Hoge, G.; Wu, H-P.; Kissel, W. S.; Pflum, D. A.; Greene, D. J.; Bao, J. J. Am. Chem. Soc. 2004, 126, 5966-5977.
15. (j) Fu, Y.; Hou, G.-H.; Xie, J.-H.; Xing, L.; Wang, L.-X.; Zhou, Q.-L. J. Org. Chem. 2004, 69, 8157-8160.
16. (k) Wu, S.; Zhang, W.; Zhang, Z.; Zhang, X. Org. Lett. 2004, 6, 3565-3567.
17. Hu, X.-P.; Zheng, Z. Org. Lett. 2004, 6, 3585-3588.
18. (m) Imamoto, T.; Oohara, N.; Takahashi, H. Synthesis 2004, 1353-1358.
19. (n) Imamoto, T.; Crépy, K. V. L.; Katagiri, K. Tetrahedron: Asymmetry 2004, 15, 2213-2218.
20. (o) Cheng, X.; Zhang, Q.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2005, 44, 1118-1121.
21. (p) Pàmies, O.; Diéguez, M.; Claver, C. J. Am. Chem. Soc. 2005, 127, 3646-3647.
22. Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, R; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998. 120, 1635-1636.
23. Gridnev, I. D.; Yamanoi, Y.; Higashi, N.; Tsuruta, H.; Yasutake, M.; Imamoto, T. Adv. Synth. Catal. 2001, 343, 118-136.
24. Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988-2989.
25. (a) Gridnev, I. D.; Higashi, N.; Asakura, K.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 7183-7194.
26. (b) Gridnev, I. D.; Yasutake, M.; Higashi, N.; Imamoto, T. J. Am. Chem. Soc. 2001, 123, 5268-5276.
27. (c) Gridnev, I. D.; Imamoto, T. Acc. Chem. Res. 2004, 37, 633-644.
28. Nagata, K.; Matsukawa, S.; Imamoto, T. J. Org. Chem. 2000, 65, 4185-4188.
29. Both t-Bu-BisP* and t-Bu-MiniPhos afford excellent enantiomeric excesses up to 99.7% only in the reductions of E-isomers. Yasutake, M.; Gridnev, I. D.; Higashi, N.; Imamoto, T. Org. Lett. 2001, 3, 1701-1704.
30. Gridnev, I. D.; Higashi, N.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 10486-10487.
31. Gridnev, I. D.; Yasutake, M.; Hogashi, N.; Imamoto, T. J. Am. Chem. Soc. 2001, 123, 5268-5276.
32. Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142-5143.
33. Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084-6085.
34. (a) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579-5580.
35. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957-6961.
36. (c) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052-5058.
37. (d) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508-11509.
38. (e) Hayashi, T. Pure Appl. Chem. 2004, 76, 465-475.
39. (f) Hayashi, T.; Yamazaki, K. Chem. Rev. 2003, 103, 2829-2844.
40. (g) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196 and references therein.
41. (a) Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc, 2000, 122, 1804-1805.
42. (b) Lautens, M.; Hiebert, S.; Renaud, J.-L. Org. Lett. 2000, 2, 1971-1973.
43. (c) Lautens, M.; Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437-1447.
44. (d) Cabrera, S.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2004, 43, 3944-3947.
45. (e) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48-58 and references therein.