Synthesis of tunable bisphosphine ligands and their application in asymmetric hydrogenation of quinolines

Journal of Organic Chemistry

Volumn 73, Issue 14, 2008, Pages 5640-5642

  Wang, Xiao Bing ^a   Zhou, Yong Gui ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; CHEMICAL REACTIONS; COMPLEXATION; HYDROGENATION; IRIDIUM; POLYETHYLENE GLYCOLS;

AMERICAN CHEMICAL SOCIETY (ACS); ASYMMETRIC HYDROGENATION; BISPHOSPHINE; CATALYST SYSTEMS; CHEMICAL EQUATIONS; IR COMPLEXES;

LIGANDS;

LIGAND; PHOSPHINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; HYDROGENATION; SYNTHESIS;

CATALYSIS; HYDROGENATION; LIGANDS; METHYLATION; MOLECULAR STRUCTURE; PHOSPHINES; QUINOLINES; STEREOISOMERISM;

EID: 48249121516     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800779r     Document Type: Article

References (50)

1. For some recent books, see:(a) Ojima, I. Ed. Catalytic Asymmetric Synthesis; Wiley-VCH: New York, 2000.
2. (b) Noyori, R. Ed. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. (c) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Eds. Comprehensive Asymmetric Catalysis; Springer: Berlin, Germany, 1999; Vols. 1-3.
4. (a) Knowles, W , S. Angew. Chem., Int. Ed. 2002, 41, 1998.
5. (b) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
6. (c) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
7. (d) Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272.
8. (a) Li, Y.-M.; Kwong, F.-Y.; Yu, W.-Y.; Chan, A. S. C. Coord. Chem. Rev. 2007, 251, 2119.
9. (b) Zhang, W.; Chi, Y.; Zhang, X. Acc. Chem. Res. 2007, 40, 1278.
10. (c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
11. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
12. (b) Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
13. (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
14. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Helv. Chim. Acta 1988, 71, 897.
15. (a) Schmid, R.; Foricher, J.; Cereghetti, M.; Schonholzer, P. Helv. Chim. Acta 1991, 74, 370.
16. (b) Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricehr, J.; Lalonde, M.; Muller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131.
17. Zhang, Z.-G.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223.
18. (a) Pai, C.-C.; Lin, C.-W.; Lin, C.-C.; Chen, C.-C.; Chan, A. S. C.; Wong, W. T. J. Am. Chem. Soc. 2000, 122, 11513.
19. (b) Wu, J.; Chen, H.; Kwok, W.-H.; Guo, R.-W.; Zhou, Z.-Y.; Yeung, C.-H.; Chan, A. S. C. J. Org. Chem. 2002, 67, 7908.
20. (c) Wu, J.; Chen, H.; Kwok, W-H.; Lam, K.-H.; Zhou, Z.-Y.; Yeung, C.-H.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 1539.
21. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
22. Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Angew. Chem., Int. Ed. 2004, 43, 320.
23. (a) Wan, X.-B.; Sun, Y.-H.; Luo, Y.-F.; Li, D.; Zhang, Z.-G. J. Org. Chem. 2005, 70, 1070.
24. (b) Sun, Y.-H.; Wan, X.-B.; Guo, M.-J.; Wang, D.-H.; Dong, X.-C.; Pan, Y.; Zhang, Z.-G. Tetrahedron: Asymmetry 2004, 15, 2185.
25. (c) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Deschaux, G.; Dellis, P. Org. Process Res. Dev. 2003, 7, 399.
26. (d) Lerouxa, F. R.; Mettler, H. Adv. Synth. Catal. 2007, 349, 323.
27. For PEG-supported chiral catalysts for asymmetric hydrogenation reactions, see: (a) Li, X.; Chen, W.; Hems, W.; King, F.; Xiao, J. Org. Lett. 2003, 5, 4559.
28. (b) Saluzzo, C.; Lamouille, T.; Herault, D.; Lemaire, M. Bioorg. Med. Chem. Lett. 2002, 12, 1841.
29. (c) Fan, Q.; Deng, G.; Lin, C.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1241.
30. (d) Fan, Q.; Deng, G.; Chen, X.; Xie, W.; Jiang, D.; Liu, D.; Chan, A. S. C. J. Mol. Catal. A: Chem. 2000, 159, 37.
31. (e) Chai, L.; Chen, H.; Li, Z.; Wang, Q.; Tao, F. Synlett 2006, 15, 2395.
32. (f) Hu, X.-P.; Huang, J.-D.; Zeng, Q.-H.; Zheng, Z. Chem. Commun. 2006, 293.
33. For our recent work on asymmetric hydrogenation of quinolines and isoquinolines, see: (a) Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357.
34. (b) Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.
35. (c) Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Adv. Synth. Catal. 2004, 346, 909.
36. (d) Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2006, 45, 2260.
37. (e) Zhao, Y.-J.; Wang, Y.-Q.; Zhou, Y.-G. Chin. J. Catal. 2005, 26, 737.
38. (f) Wang, D.-W.; Zeng, W.; Zhou, Y.-G. Tetrahedron: Asymmetry 2007, 18, 1103.
39. For other group's work on asymmetric hydrogenation of quinolines, see: (a) Xu, L.-J.; Lam, K.-H.; Ji, J.-X.; Wu, J.; Fan, Q.-H.; Lo, W.-H.; Chan, A. S. C. Chem. Commun. 2005, 1390.
40. (b) Lam, K.-H.; Xu, L.-J.; Feng, L.-C.; Fan, Q.-H.; Lam, F.-L.; Lo, W.-H.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1755.
41. (c) Yamagata, T.; Tadaoka, H.; Nagata, M.; Hirao, T.; Kataoka, Y.; Ratovelomanana-Vidal, V.; Genet, J. P.; Mashima, K. Organometallics 2006, 25, 2505.
42. (d) Reetz, M. T.; Li, X. Chem. Commun. 2006, 2159.
43. (e) Wu, J.; Chan, A. S. C. Acc. Chem. Res. 2006, 39, 711.
44. (f) Tang, W.-J.; Zhu, S.-F.; Xu, L.-J.; Zhou, Q.-L.; Fan, Q.-H.; Zhou, H.-F.; Lam, K.-H.; Chan, A. S. C. Chem. Commun 2007, 613.
45. (g) Qiu, L.-Q.; Kwong, F.-Y.; Wu, J.; Lam, W.-H.; Chan, S.-S.; Yu, W.-Y.; Li, Y.-M.; Guo, R.-W.; Zhou, Z.-Y.; Chan, A. S. C. J. Am. Chem. Soc. 2006, 128, 5955.
46. (h) Wang, Z.-J.; Deng, G.-J.; Li, Y.; He, Y.-M.; Tang, W.-J.; Fan, Q.-H. Org. Lett. 2007, 9, 1243.
47. (i) Chan, S.-H.; Lam, K.-H.; Li, Y.-M.; Xu, L.-J.; Tang, W.-J.; Lam, F.-L.; Lo, W.-H.; Yu, W.-Y.; Fan, Q.-H.; Chan, A. S. C. Tetrahedron: Asymmetry 2007, 18, 2625.
48. (j) Jahjah, M.; Alame, M.; Pellet-Rostaing, S.; Lemaire, M. Tetrahedron: Asymmetry 2007, 18, 2305.
49. Asymmetric transfer hydrogenation of quinolines with organocatalysis, see: (a) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
50. (b) Guo, Q.-S.; Du, D.-M.; Xu, J.-X. Angew. Chem., Int. Ed. 2008, 47, 759.