Reversal in enantioselectivity for the palladium-catalyzed asymmetric allylic substitution with novel metallocene-based planar chiral diphosphine ligands

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 1012-1015

  Xie, Fang ^a   Liu, Delong ^a   Zhang, Wanbin ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BIS(OXAZOLINYL) 2,2' DIPHENYLPHOSPHINO METALLOCENE; 1,1' DIHYDROXYMETHYL 2,2' DIPHENYLPHOSPHINO METALLOCENE; PALLADIUM; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; SUBSTITUTION REACTION;

EID: 37849039728     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.009     Document Type: Article

References (48)

1. Kimura K., Sugiyama E., Ishizuka T., and Kunieda T. Tetrahedron Lett. 33 (1992) 3147-3150
2. Hoarau O., Ait-Haddou H., Daran J.-C., Cramailere D., and Balavoine G.G.A. Organometallics 18 (1999) 4718-4723
3. Evans D.A., Johnson J.S., Burgey C.S., and Campos K.R. Tetrahedron Lett. 40 (1999) 2879-2882
4. Sibi M.P., Chen J., and Cook G.R. Tetrahedron Lett. 40 (1999) 3301-3304
5. Chelucci G., Pinna G.A., Saba A., and Valenti R. Tetrahedron: Asymmetry 11 (2000) 4027-4036
6. Li X.-G., Cheng X., Ma J.-A., and Zhou Q.-L. J. Organomet. Chem. 640 (2001) 65-71
7. Sibi M.P., and Liu M. Curr. Org. Chem. 5 (2001) 719-755
8. Cobb A.J.A., and Marson C.M. Tetrahedron: Asymmetry 12 (2001) 1547-1550
9. Cobb A.J.A., and Marson C.M. Tetrahedron 61 (2005) 1269-1279
10. Frolander A., Lutsenko S., Privalov T., and Moberg C. J. Org. Chem. 70 (2005) 9882-9891
11. Selected reviews:. In: Hayashi T., and Togni A. (Eds). Ferrocenes (1995), Wily-VCH, Weinheim, Germany
12. In: Togni A., and Haltermann R.L. (Eds). Metallocenes (1998), Wiley-VCH, Weinheim, Germany
13. Dai L.-X., Tu T., You S.L., Deng W.P., and Hou X.-L. Acc. Chem. Res. 36 (2003) 659-667
14. Colacot T.J. Chem. Rev. 103 (2003) 3101-3118
15. Arrays R.G., Adrio J., and Carretero J.C. Angew. Chem., Int. Ed. 45 (2006) 7674-7715
16. Selected papers:. Zhang W., Yoneda Y.-I., Kida T., Nakatsuji Y., and Ikeda I. Tetrahedron: Asymmetry 9 (1998) 3371-3380
17. Zhang W., Yoneda Y.-I., Kida T., Nakatsuji Y., and Ikeda I. J. Organomet. Chem. 574 (1999) 19-23
18. Imai Y., Zhang W., Kida T., Nakatsuji Y., and Ikeda I. Chem. Lett. (1999) 243-244
19. Zhang W., Yoshinaga H., Imai Y., Kida T., Nakatsuji Y., and Ikeda I. Synlett (2000) 1512-1514
20. Zhang W., Xie F., Yoshinaga H., Kida T., Nakatsuji Y., and Ikeda I. Tetrahedron 62 (2006) 9038-9042
21. Hua G.H., Liu D.L., Xie F., and Zhang W. Tetrahedron Lett. 48 (2007) 385-388
22. Zheng W.-H., Zheng B.-H., Zhang Y., and Hou X.-L. J. Am. Chem. Soc. 129 (2007) 7718-7719
23. Zhang W., Adachi Y., Hirao T., and Ikeda I. Tetrahedron: Asymmetry 7 (1996) 451-460
24. Zhang W., Hirao T., and Ikeda I. Tetrahedron Lett. 37 (1996) 4545-4548
25. Liu D.L., Xie F., and Zhang W. Tetrahedron Lett. 48 (2007) 585-588
26. Liu D.L., Xie F., and Zhang W. Tetrahedron Lett. 48 (2007) 7591-7594
27. Liu, D, L.; Xie, F.; Zhang, W. Tetrahedron, submitted for publication.
28. Zhang W., Kida T., Nakatsuji Y., and Ikeda I. Tetrahedron Lett. 37 (1996) 7995-7998
29. Zhang W., Shimanuki T., Kida T., Nakatsuji Y., and Ikeda I. J. Org. Chem. 64 (1999) 6247-6251
30. Liu D.L., Xie F., and Zhang W. J. Org. Chem. 72 (2007) 6992-6997
31. 2Fe 614.1231, found 614.12215.
32. 2Ru 660.0915, found 660.09156.
33. 2Fe 698.1457, found 698.14328.
34. 2Ru 744.1139, found 744.11269.
35. 2Fe 642.1556, found 642.15345.
36. 2Ru 688.1234, found 688.12286.
37. For reviews:. Trost B.M. Chem. Pharm. Bull. 50 (2002) 1-14
38. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921-2943
39. For papers:. Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., and Yanagi K. J. Am. Chem. Soc. 111 (1989) 6301-6311
40. Trost B.M., and Bunt R.C. J. Am. Chem. Soc. 116 (1994) 4089-4090
41. Evans D.A., Campos K.R., Tedrow J.S., Michael F.E., and Gagne M.R. J. Org. Chem. 64 (1999) 2994-2995
42. You S.-L., Zhu X.-Z., Lou Y.-M., Hou X.-L., and Dai L.-X. J. Am. Chem. Soc. 123 (2001) 7471-7472
43. Mori M., Nakanishi M., Kajishima D., and Sato Y. J. Am. Chem. Soc. 125 (2003) 9801-9807
44. Uozumi Y., Tanaka H., and Shibatomi K. Org. Lett. 6 (2004) 281-283
45. Takahashi K., Nakano H., and Fujita R. Tetrahedron Lett. 46 (2005) 8927-8930
46. Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., and Yanagi K. J. Am. Chem. Soc. 111 (1989) 6301-6311
47. Ait-Haddou H., Hoarau O., Cramailere D., Pezet F., Daran J.-C., and Balavoine G.G.A. Chem. Eur. J. 10 (2004) 699-707
48. Wimmer P., and Widhalm M. Tetrahedron: Asymmetry 6 (1995) 657-660