An improved method for the synthesis of optically active tomoxetines and fluoxetines

Chinese Journal of Chemistry

Volumn 22, Issue 8, 2004, Pages 775-778

  Xu, Cheng Fu ^a   Yuan, Cheng Ye ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

3 hydroxy 3 arylpropionate; 3 hydroxy 4,4,4 trifluorobutanoate; Candia rugosa lipase (CRL); Fluoxetine; Tomoxetine

Indexed keywords

3 HYDROXY 4,4,4 TRIFLUOROBUTANOATE; ANTIDEPRESSANT AGENT; ATOMOXETINE; BELOXATONE; BUTYRIC ACID DERIVATIVE; FLUOXETINE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; OPTICS;

EID: 5044237443     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20040220802     Document Type: Article

References (62)

1. (a) Foster, B. J.; Lavagnino, E. R. Drugs of the Future, Vol. 11, Prous Science Publishers, Barcelona, Spain, 1986, p. 134.
2. (b) Robertson, D. W.; Krushins, J. H.; Fuller, R. W.; Leander, J. D. J. Med. Chem. 1988, 31, 1412.
3. Ankier, S. I. Prog. Med. Chem. 1986, 23, 121.
4. (a) Srebnick, M.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1988, 53, 2916.
5. (b) Gao, Y.; Sharpless, K. B. J. Org. Chem. 1988, 53, 4801.
6. (c) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5207.
7. (d) Kumar, A.; Ner, D. H.; Dike, S. Y. Tetrahedron Lett. 1991, 32, 1901.
8. (e) Fronza, G.; Fuganti, C.; Grasselli, P.; Mele, A. J. Org. Chem. 1991, 56, 6019.
9. (f) Chenevert, R.; Fortier, G.; Rhlid, R. B. Tetrahedron 1992, 48, 6769.
10. (g) Koenig, T. M.; Mitchell, D. Tetrahedron 1994, 35, 1339.
11. (a) Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
12. (b) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron: Asymmetry 2002, 13, 2605.
13. (c) Ireland, T.; Grossheimann, G.; Wieser, J. C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212.
14. (d) Wu, J.; Chen, H.; Kwok, W. H.; Lam, K. H.; Zhou, Z. Y.; Yeung, C. H.; Chan, Albert S. C. Tetrahedron Lett. 2002, 43, 1539.
15. (e) Ratovelomanana, V. V.; Genet, J. P. J. Organomet. Chem. 1998, 567, 163.
16. (f) Bardot, V.; Besse, P.; Gelas-Miahle, Y.; Remuson, R.; Veschambre, H. Tetrahedron: Asymmetry 1996, 7, 1077.
17. (g) Manzocchi, A.; Casati, R.; Fiecchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1 1987, 2753.
18. (h) Deol, B. S.; Ridley, D. D.; Simpson, G. W. Aust. J. Chem. 1976, 29, 2459.
19. (i) Soai, K.; Yamanoi, T.; Hikima, H.; Oyamada, H. J. Chem. Soc., Chem. Commun. 1985, 138.
20. (j) Mukaiyama, T.; Tomimori, K.; Oriyama, T. Chem. Lett. 1955, 813.
21. (k) Hilborn, J. W.; Lu, Z. H.; Jurgens, A. R.; Fang, K. Q.; Byers, P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2001, 42, 8919.
22. (a) Mioskowski, C.; Solladie, G. Tetrahedron 1980, 36, 227.
23. (b) Evans, D. A.; Taber, T. R. Tetrahedron Lett. 1980, 21, 4675.
24. (c) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
25. (d) Braun, M.; Devant, R. Angew. Chem., Int. Ed. Engl. 1953, 95, 802.
26. (e) Bernardi, A.; Colombo, L.; Gennarri, C.; Prati, L. Tetrahedron 1984, 40, 3759.
27. (f) Braun, M.; Devant, R. Tetrahedron 1984, 25, 5031.
28. (g) Hemchen, G.; Leikauf, U.; Taufer-Knopfel, I. Angew. Chem., Int. Ed. Engl. 1985, 97, 874.
29. (h) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. J. Am. Chem. Soc. 1986, 108, 8279.
30. (i) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397.
31. (a) Guette, M.; Capillon, J.; Guette, J. P. Tetrahedron 1973, 29, 3659.
32. (b) Seebach, D.; Langer, W. Helv. Chim. Acta 1979, 62, 1701.
33. (c) Basile, T.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1989, 596.
34. (d) Basavaiah, D.; Bharathi, T. K. Synth. Commun. 1959, 19, 2035.
35. (e) Basavaiah, D.; Bharathi, T. K. Tetrahedron Lett. 1991, 32, 3417.
36. (f) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781.
37. (a) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 6968.
38. (b) Bednarski, M.; Maring, K.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451.
39. Oppoler, W.; Mills, R. J.; Pachinger, W.; Stevenson, T. Helv. Chim. Acta 1986, 69, 1542.
40. Ali, H. S.; Sudalai, A. Tetrahedron Lett. 2002, 43, 5435.
41. (a) Boaz, N. W. J. Org. Chem. 1992, 57, 4289.
42. (b) Schneider, M. P.; Goergous, U. Tetrahedron: Asymmetry 1992, 3, 525.
43. (c) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253.
44. (d) Liu, H. L.; Hoff, B. H.; Anthonsen, T. J. Chem. Soc., Perkin Trans. 1 2000, 1767.
45. (e) Kamal, A.; Ramesh, G. B.; Ramu, R. Tetrahedron: Asymmetry 2002, 13, 2039.
46. (a) Yuan, C. Y.; Wang, K.; Li, Z. Y. Heteroat. Chem. 2001, 12, 551.
47. (b) Yuan, C. Y.; Wang, K.; Li, Z. Y. Heteroat. Chem. 2002, 13, 153.
48. (c) Wang, K.; Li, J. F.; Yuan, C. Y.; Li, Z. Y. Chin. J. Chem. 2002, 20, 1379.
49. (a) Zhang, Y. H.; Li, Z. Y.; Yuan, C. Y. Tetradedron Lett. 2002, 43, 3247.
50. (b) Zhang, Y. H.; Li, J. F.; Yuan, C. Y. Tetrahedron 2003, 59, 473.
51. (c) Zhang, Y. H.; Xu, C. F.; Li, J. F.; Yuan, C. Y. Tetrahedron: Asymmetry 2003, 14, 63.
52. (d) Yuan, C. Y.; Xu, C. F.; Zhang, Y. H. Tetrahedron 2003, 59, 6095.
53. (e) Zhang, Y. H.; Yuan, C. Y.; Li, Z. Y. Tetrahedron 2002, 58, 2973.
54. (a) Bucciarell, M.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Biocatalysis 1994, 9, 313.
55. (b) Seebach, D.; Renaud, P.; Schweizer, W. B.; Zueger, M. F.; Brienne, M. J. Helv. Chim. Acta 1984, 67, 1483.
56. (c) Gotzo, S. P.; Seebach, D.; Sanglier, J. J. Eur. J. Org. Chem. 1999, 2533.
57. (d) Antolini, I.; Forni, A.; Davoli, P.; Moretti, I.; Prati, F. Tetrahedron: Asymmetry 1998, 9, 285.
58. Cohen, S. C.; Khedouri, E. J. Am. Chem. Soc. 1961, 83, 4228.
59. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Shi, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
60. (a) Goetzoe, S. P.; Seebach, D.; Sanglier, J. J. Eur. J. Org. Chem. 1999, 10, 2533.
61. (b) Seebach, D.; Renaud, P.; Schweizer, B.; Zueger, M. F.; Brienne, M. J. Helv. Chim. Acta 1994, 67, 1843.
62. (c) Seebach, D.; Beck, A. K.; Renaud, P. Angew. Chem., Int. Ed. Engl. 1986, 98, 96.