Air-stable Ir-(P-Phos) complex for highly enantioselective hydrogenation of quinolines and their immobilization in poly(ethylene glycol) dimethyl ether (DMPEG)

Chemical Communications

Volumn , Issue 11, 2005, Pages 1390-1392

  Xu, Lijin ^a   Lam, Kim Hung ^a   Ji, Jianxin ^a   Wu, Jing ^a   Fan, Qing Hua ^b   Lo, Wai Hung ^a   Chan, Albert S C ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM COMPLEX; MACROGOL DERIVATIVE; PHOSPHORUS DERIVATIVE; POLYETHYLENE GLYCOL DIMETHYL ETHER; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC HYDROGENATION; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION;

EID: 16644386624     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b416397d     Document Type: Article

References (42)

1. P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis; Academic Press, New York, 1979, p 175.
2. (a) H.-U. Blaser, C. Malan, B. Pugin, F. Splindler, H. Steiner and M. Studer. Adv. Synth. Catal., 2003, 345, 103;
3. (b) W. Tang and X. Zhang, Chem. Rev., 2003, 103, 3029;
4. (c) G. Q. Lin, Y. M. Li and A. S. C. Chan, Principles and Applications of Asymmetric Synthesis; Wiley-Interscience, New York, 2001.
5. For some recent publications, see (a) J. P. Henschke, M. J. Burk, C. G. Malan, D. Herzberg, J. A. Peterson, A. J. Wildsmith, C. J. Cobley and G. Casy, Adv. Synth. Catal., 2003, 345, 300;
6. (b) R. Kuwano, K. Kaneda, T. Ito, K. Sato, T. Kurokawa, D. Karube and Y. Ito, J. Org. Lett., 2004, 6, 2213.
7. (a) W. Wang, S. Lu, P. Yang, X. Han and Y. Zhou, J. Am. Chem. Soc., 2003, 125, 10536;
8. (b) P. Yang and Y. Zhou, Tetrahedron: Asymmetry, 2004, 15, 2222;
9. (c) S. Lu, X. Han and Y. Zhou, Adv. Synth. Catal., 2004, 346, 909.
10. J. G. Keay, in Comprehensive Organic Synthesis; ed. B. M. Trost and I. Fleming, Pergamon: Oxford, 1991, vol. 8, p 579
11. (a) A. R. Kartritzky, S. Rachwal and B. Rachwal, Tetrahedron, 1996, 52, 15031;
12. (b) Comprehensive Natural Products Chemistry, D. H. Barton, K. Nakanishi and O. Meth-Cohn, Elsevier, Oxford, 1999; vol. 1-9.
13. (a) C.-C. Pai, C.-W. Lin, C.-C. Lin, C.-C. Chen and A. S. C. Chan. J. Am. Chem. Soc., 2000, 122, 11513;
14. (b) J. Wu, H. Chen, Z. Zhou, C.-H. Yeung and A. S. C. Chan, Synlett, 2001, 1050;
15. (c) J. Wu, H. Chen, W. H. Kwok, K. H. Lam, Z. Zhou, C.-H. Yeung and A. S. C. Chan, Tetrahedron Lett., 2002, 43, 1539;
16. (d) J. Wu, H. Chen, W. H. Kwok, R. Guo, Z. Zhou, C.-H. Yeung and A. S. C. Chan, J. Org. Chem., 2002, 67, 7908;
17. (e) J. Wu, X. Chen, R. Guo, C.-H. Yeung and A. S. C. Chan, J. Org. Chem., 2003, 68, 2490;
18. (f) J. Wu, J. Ji, R. Guo, C.-H. Yeung and A. S. C. Chan, Chem. - Eur. J., 2003, 9, 2963.
19. (a) Q. Fan, Y. Li and A. S. C. Chan, Chem. Rev., 2002, 102, 3385;
20. (b) Q. Fan, C. Ren, C.-H. Yeung, W. Hu and A. S. C. Chan, J. Am. Chem. Soc., 1999, 121, 7407;
21. (c) Q. Fan, Y. Chen, X. Chen, D. Jiang, F. Xi and A. S. C. Chan, Chem. Commun., 2000, 789;
22. (d) Q. Fan, G. Deng, C. Lin and A. S. C. Chan, Tetrahedron: Asymmetry, 2001, 12, 1241;
23. (e) G. Deng, Q. Fan, X. Chen, D. Liu and A. S. C. Chan, Chem. Commun., 2002, 1570;
24. (f) B. Yi, Q. Fan, G. Deng, Y. Li, L. Qiu and A. S. C. Chan, Org. Lett., 2004, 6, 1361.
25. For recent reviews, see (a) C. E. Song, Chem. Commun., 2004, 1033;
26. (b) C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumon and J.-C. Plaquevent, Tetrahedron: Asymmetry, 2003, 14, 3081,
27. For recent examples, see: (c) A. Hu, H. Ngo and W. Lin, Angew. Chem. Int. Ed., 2004, 43, 2501;
28. (d) Y. Zhu, K. Carpenter, C. B. Ching, S. Bahnmueller, P. K. Chan, V. S. Srid, W. K. Leong and M. F. Hawthrone, Angew. Chem. Int. Ed., 2003, 42, 3792;
29. (e) S.-G. Lee, Y. J. Zhang, J. Y. Piao, H. Yoon, C. E. Song, J. H. Choi and J. Hong, Chem. Commun., 2003, 2624;
30. (f) H. Ngo, A. Hu and W. Lin, Chem. Commun., 2003, 1912;
31. (g) P. G. Jessop, R. R. Stanley, R. Brown, C. A. Eckert, C. L. Liotta, T. T. Ngo and P. Pollet, Green Chem., 2003, 5, 3.
32. (a) R. G. da Rosa, L. Martinelli, L. H. M. da Silva and W. Loh, Chem. Commun., 2000, 33;
33. (b) D. J. Heldebrant and P. G. Jessop, J. Am. Chem. Soc., 2003, 125, 5600;
34. (c) W. Lertner, Nature, 2003, 423, 930;
35. (d) A. Haimov and R. Neumann, Chem. Commun., 2002, 876;
36. (e) S. Chandrasekhar, Ch. Narsihmulu, S. S. Sultana and N. R. Reddy, Org. Lett., 2002, 4, 4399;
37. (f) S. Chandrasekhar, C. Narsihmulu, S. S. Sultana and N. R. Reddy, Chem. Commun., 2003, 1716;
38. (g) S. Chandrasekhar, C. Narsihmulu, G. Chandrashekar and T. Shyamsunder, Tetrahedron Lett., 2004, 45, 2421;
39. (h) P. C. Andrew, A. C. Peatt and C. L. Raston, Green Chem., 2004, 6, 119;
40. (i) R. Jiang, Y. Kuang, X. Sun and S. Zhang, Tetrahedron: Asymmetry, 2004, 15, 743;
41. (j) S. Chandrasekhar, C. Narsihmulu, B. Saritha and S. S. Sultana, Tetrahedron Lett., 2004, 45, 5865.
42. D. Hou, J. Reibenspies, T. J. Colacot and K. Burgess, Chem. Eur. J., 2001, 7, 5391.