Asymmetric hydrogenation of imines catalyzed by Ir/phosphine-oxazoiine complexes with an axis-unfixed biphenyl backbone

Chinese Journal of Organic Chemistry

Volumn 31, Issue 4, 2011, Pages 505-510

  Yao, Dongmei ^a   Tian, Fengtao ^a   Zhang, Wanbin ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

Asymmetric hydrogenation.; Axial chirality; Imine; Ir complex.; Phosphine oxazoline ligand

Indexed keywords

EID: 79960796733     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
2. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
3. Schmid, R.; Ceregheti, M.; Heiser, B.; Schonholzer, P.; Hansan, H. J. Helv. Chim. Acta 1988, 71, 897.
4. Murata, M.; Morimoto, T. K. Synlett 1991, 827.
5. Schimid, R.; Foricher, J.; Cereghetti, M.; Schonholzer, P. Helv. Chim. Acta 1991, 74, 370.
6. Yamamoto, W.; Murata, M.; Morimoto, S.; Achiwa, K. Chem. Pharm. Bull. 1991, 39, 1085.
7. Jendralla, H.; Li, C. H.; Paulaus, E. Tetrahedron: Asymmetry 1994, 5, 1297.
8. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1997, 38, 2681.
9. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 2000, 65, 3326.
10. Zhang, W.; Xie, F.; Matsuo, S.; Imahori, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 2006, 17, 161.
11. Wang, F.; Zhang, Y. J.; Yang, G.; Zhang, W. Tetrahedron Lett. 2007, 48, 4179.
12. Zhang, J. M.; Zhang, Y. J.; Zhang, W. B. Chin. J. Org. Chem. 2007, 27, 1089 (in Chinese).
13. Dai, Y. J.; Yang, G. Q.; Zhang, Y. J.; Wang, F. J.; Zhang, W. B. Chin. J. Org. Chem. 2008, 28, 1169 (in Chinese).
14. Zhang, W.; Xie, F.; Yoshinaga, H.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 2006, 1185.
15. Tian, F.; Yao, D.; Zhang, Y. J.; Zhang, W. Tetrahedron 2009, 65, 9609.
16. Lu, S. M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 8920.
17. Lu, W. J.; Chen, Y. W.; Hou, X. L. Angew. Chem., Int. Ed. 2008, 47, 10133.
18. Zhang, Y.; Han, Z. B.; Li, F. Y.; Ding, K. L.; Zhang, A. Chem. Commun. 2010, 46, 156.
19. Part of the complexation behavior of the ligands with Ir(I) has been communicated: Tian, F.; Yao, D.; Liu, Y; Xie, F.; Zhang, W. Adv. Synth. Catal. 2010, 352, 1841.
20. Liu, Y; Yang, G.; Yao, D.; Tian, F.; Zhang, W. Sci. China, Sen B: Chem. 2011, 54, 87.
21. Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C; Pfaltz, A. Chem. Eur. J. 1997, 3, 887.
22. Lightfood, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2891.
23. Zhu, S. F.; Xie, J. B.; Zhang, Y. Z.; Li, S.; Zhou, Q. L. J. Am. Chem. Soc. 2006, 128, 12886.
24. Blaser, H. U.; Spindler, F. In Comprehensive Asymmetric Catalysis, Vol. 1, Eds.: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Springer, Berlin, 1999, p. 247.
25. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
26. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
27. Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C; Pfaltz, A. Chem. Eur. J. 1997, 3, 887.
28. Lightfood, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2897.
29. Cozzi, P. G.; Menges, F.; Kaiser, S. Synlett 2003, 833.
30. Blanc, C; Agbossou-Niedercorn, F.; Nowogrocki, G. Tetrahedron: Asymmetry 2004, 15, 2159.
31. Moessner, C; Bolm, C. Angew. Chem., Int. Ed. 2005, 44, 7564.
32. Trifonova, A.; Diesen, J. S.; Andersson, P. G. Chem. Eur. J. 2006, 72, 2318.
33. Zhu, S. F.; Xie, J. B.; Zhang, Y. Z.; Li, S.; Zhou, Q. L. J. Am. Chem. Soc. 2006,128, 12886.
34. Cheemala, M. N.; Knochel, P. Org. Lett. 2007, 9, 3089.
35. Han, Z.; Wang, Z.; Zhang, X; Ding, K. Angew. Chem., Int. Ed. 2009, 48, 5345.