Preparation of polymer-supported Ru-TsDPEN catalysts and use for enantioselective synthesis of (S)-fluoxetine

Organic and Biomolecular Chemistry

Volumn 3, Issue 14, 2005, Pages 2513-2518

  Li, Yangzhou ^a   Li, Zhiming ^a   Li, Feng ^a   Wang, Quanrui ^a   Tao, Fanggang ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; HYDROGENATION; KETONES; ORGANIC POLYMERS; PROTEINS; SUBSTRATES; SYNTHESIS (CHEMICAL); TOXICITY;

AROMATIC KETONES; ENANTIOSELECTIVE SYNTHESIS; FLUOXETINE; TOXIC TRANSITION;

CATALYSTS;

1,2 DIANILINOETHANE; 1,2-DIANILINOETHANE; 4 CYMENE; 4-CYMENE; DRUG DERIVATIVE; ETHYLENEDIAMINE DERIVATIVE; FLUOXETINE; POLYMER; RUTHENIUM; SEROTONIN UPTAKE INHIBITOR; TERPENE; TOLUENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; ETHYLENEDIAMINES; FLUOXETINE; MOLECULAR STRUCTURE; MONOTERPENES; POLYMERS; RUTHENIUM; SEROTONIN UPTAKE INHIBITORS; STEREOISOMERISM; TOLUENE;

EID: 23044484402     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b505943g     Document Type: Article

References (43)

1. D. W. Roberson, J. H. Krushinski, R. W. Fuller and J. D. Leander, J. Med. Chem., 1988, 31, 1412 and references cited therein.
2. H. Silver, Int. Clin. Psychopharm., 2003, 18, 305.
3. (a) R. Chénevert and G. Fortier, Chem. Lett., 1991, 1603;
4. (b) R. Chénevert, G. Fortier and R. B. Rhlid, Tetrahedron, 1992, 48, 6769.
5. (a) S. Sakuraba and K. Achiwa, Chem. Pharm. Bull., 1995, 43, 748;
6. (b) Lily Co, Drugs Future, 1996, 21, 83.
7. (a) H. E. Master, R. V. Newadkar, R. A. Rane and A. Kumar, Tetrahedron Lett., 1996, 37, 9253;
8. (b) M. Quirós, F. Rebolledo, R. Liz and V. Gotor, Tetrahedron: Asymmetry, 1997, 8, 3035.
9. (a) E. J. Corey and G. A. Reichard, Tetrahedron Lett., 1989, 30, 5207;
10. (b) S. Sakuraba and K. Achiwa, Synlett, 1991, 689;
11. (c) A. Kumar, D. H. Ner and S. Y. Dike, Tetrahedron Lett., 1991, 32, 1901;
12. (d) U. T. Bhalerao, Y. Chandraprakash, R. L. Babu and N. W. Fadnavis, Syn. Commun., 1993, 23, 1201;
13. (e) T. M. Koenig and D. Mitchell, Tetrahedron Lett., 1994, 35, 1339;
14. (f) P. N. Devine, R. M. Heid and D. M. Tschaen, Tetrahedron, 1997, 53, 6739;
15. (g) H.-L. Huang, L. T. Liu, S.-F. Chen and H. Ku, Tetrahedron: Asymmetry, 1998, 9, 1637;
16. (h) J. W. Hilborn, Z.-H. Lu, A. R. Jurgens, Q. Fang, K. P. Byers, S. A. Wald and C. H. Senanayaake, Tetrahedron Lett., 2001, 42, 8919;
17. (i) M. Watanabe, K. Murata and T. Ikariya, J. Org. Chem., 2002, 67, 1712;
18. (j) J. B. Ribeiro, M. D. Ramos, F. R. Neto, S. G. F. Leite and O. A. C. Antunes, Catal. Commun., 2005, 6, 131.
19. R. K. Pandey, R. A. Fernandes and P. Kumar, Tetrahedron Lett., 2002, 43, 4425.
20. W. H. Miles, E. J. Fialcowitz and E. S. Halstead, Tetrahedron, 2001, 57, 9925.
21. For reviews on asymmetric transfer hydrogenations, see: (a) H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner and M. Studer, Adv. Synth. Catal., 2003, 345, 103;
22. (b) K. Everaere, A. Mortreux and J.-F. Carpentier, Adv. Synth. Catal., 2003, 345, 67;
23. (c) C. Saluzzo and M. Lemaire, Adv. Synth. Catal., 2002, 344, 915;
24. (d) C. Saluzzo, R. ter Halle, F. Touchard, F. Fache, E. Schulz and M. Lemaire, J. Organomet. Chem., 2000, 603, 30;
25. (e) M. J. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045;
26. (f) R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97;
27. (g) G. Zassinovich, G. Mestroni and S. Gladiali, Chem. Rev., 1992, 92, 1051.
28. For reviews see(a) B. C. G. Soderberg, Coord. Chem. Rev., 2002, 224(1-2), 171;
29. (b) B. M. Bhanage and M. Arai, Catal. Rev. Sci. Eng., 2001, 43, 315;
30. (c) Y. R. de Miguel, J. Chem. Soc., Perkin Trans, 1, 2000, 24, 4213;
31. (d) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 23, 3815;
32. (e) G. Jannes and V. Dubois, Eds., Chiral Reactions in Heterogeneous Catalysis, Plenum Press, New York, 1995.
33. (a) X. Li, W. Chen, W. Hem, F King and J. Xiao, Tetrahedron Lett., 2004, 45, 951;
34. (b) P. N. Liu, P. M. Wang and Y. Q. Tu, Org. Lett., 2004, 6, 169;
35. (c) Y. C. Chen, T. F Wu, J. G. Deng, H. Liu, J. Zhu, Y. Z. Jiang, M. C. K. Choi and A. S. C. Chan, J. Org. Chem., 2002, 67, 5301;
36. (d) Y. C. Chen, T. F Wu, J. G. Deng, H. Liu, Y. Z. Jiang, M. C. K. Choiband and A. S. C. Chan, Chem. Commun., 2001, 1488;
37. (e) D. J. Bayston, C. B. Travers and M. E. C. Polywka, Tetrahedron: Asymmetry, 1998, 9, 2015.
38. S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1995, 117, 7562.
39. (a) D. Šterk, M. S. Stephan and B. Mohar, Tetrahedron: Asymmetry, 2002, 13, 2605;
40. (b) B. Mohar, A. Valleix, J.-R. Desmurs, M. Felemez, A. Wagner and C. Mioskowski, Chem. Commun., 2001, 2572;
41. (c) A. Wagner, C. Mioskowski, B. Mohar, J.-R. Desmurs, F. Le Guyader, and T. Schlama, WO 00/76942, 2000.
42. D. Mitchell and T. M. Koenig, Synth. Commun., 1995, 25, 1231.
43. A. Schneider and U. Goergens, Tetrahedron: Asymmetry, 1992, 3, 525.