Stereoselective Synthesis of Diltiazem via Dynamic Kinetic Resolution

Synthesis

Volumn , Issue 15, 2003, Pages 2405-2409

  Mordant, Céline ^a   De Andrade, Cristina Caño ^a   Touati, Ridha ^a   Ratovelomanana Vidal, Virginie ^a   Hassine, Bechir Ben ^a   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

Asymmetric catalysis; Diltiazem; Drugs; Hydrogenations; Kinetic resolution; Ruthenium

Indexed keywords

ESTERS; HYDROGENATION; MIXTURES; STEREOCHEMISTRY;

STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

DILTIAZEM; ESTER; METHYL 2 CHLORO 3 HYDROXY 3 (4 METHOXYPHENYL)PROPIONATE; PROPIONIC ACID DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; STEREOCHEMISTRY;

EID: 0242404392     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42397     Document Type: Article

References (40)

1. Centro de Ciências Exatas e Naturais, Universidade Federal de Alagoas, Campus A.C. Simões, Tabuleiro do Martins, 57072-970, Maceió, Brasil.
2. Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène, 01 UR 1201, Facultés des Sciences de Monastir, Avenue de l'Environnement, 5019 Monastir, Tunisie.
3. (a) Nagao, T.; Sato, M.; Nakajima, H.; Kiyomoto, A. Chem. Pharm. Bull. 1973, 21, 92.
4. (b) Yasue, H.; Omote, S.; Takizawa, A.; Nagao, T. Circ. Res. Suppl. 1 1983, 52.
5. (a) Bousquet, A.; Dormoy, J.-R.; Heymes, A. Sanofi, Patent EP 040912, 1991.
6. (b) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
7. (c) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622.
8. (d) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans, 1 1997, 3501.
9. (e) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621.
10. (f) Solladie-Cavallo, A.; Bouerat, L.; Jierry, L. Eur. J. Org. Chem. 2001, 66, 4557.
11. (g) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201.
12. (h) Furutani, T.; Imashiro, R.; Hatsuda, M.; Seki, M. J. Org. Chem. 2002, 67, 4599.
13. Imashiro, R.; Kuroda, T. J. Org. Chem. 2003, 68, 974.
14. (a) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851.
15. (b) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821.
16. Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643.
17. (a) Rossey, G.; Tixidre, A.; Wick, A.; Zard, L. Synthelabo, Jpn Patent 4-217969,1992.
18. (b) Yamada, S.; Morimatsu, K.; Yoshioka, R.; Osaki, Y.; Seko, H. Tetrahedron: Asymmetry 1998, 9, 1713.
19. (a) Gentile, A.; Giordano, C. J. Org. Chem. 1992, 57, 6635.
20. (b) Inoue, H.; Matsuki, K.; Oh-Ishi, T. Chem. Pharm. Bull. 1993, 41, 1521.
21. (c) Matsumae, H.; Douno, H.; Yamada, S.; Nishida, T.; Ozaki, Y.; Shibatani, T.; Tosa, T. J. Ferment. Bioeng. 1995, 79, 29.
22. (d) Desai, S. B.; Argade, N.; Ganesh, K. N. J. Org. Chem. 1996, 61, 6730.
23. (10) Reviews: (a) Genet, J.-P. In Reductions in Organic Synthesis, ACS Symposium Series 641; Magid, A., Ed.; American Chemical Society: Washington DC, 1996, 31. (b) Genet, J.-P. In Advances in Aymmetric Synthesis; Stephenson, G. R., Ed.; Chapman and Hall: London, 1996, 60. (c) Ratovelomanana-Vidal, V.; Genet, J.-P. J. Organomet. Chem. 1998, 567, 163.
24. Reviews: (a) Genet, J.-P. In Reductions in Organic Synthesis, ACS Symposium Series 641; Magid, A., Ed.; American Chemical Society: Washington DC, 1996, 31. (b) Genet, J.-P. In Advances in Aymmetric Synthesis; Stephenson, G. R., Ed.; Chapman and Hall: London, 1996, 60. (c) Ratovelomanana-Vidal, V.; Genet, J.-P. J. Organomet. Chem. 1998, 567, 163.
25. Reviews: (a) Genet, J.-P. In Reductions in Organic Synthesis, ACS Symposium Series 641; Magid, A., Ed.; American Chemical Society: Washington DC, 1996, 31. (b) Genet, J.-P. In Advances in Aymmetric Synthesis; Stephenson, G. R., Ed.; Chapman and Hall: London, 1996, 60. (c) Ratovelomanana-Vidal, V.; Genet, J.-P. J. Organomet. Chem. 1998, 567, 163.
26. (a) Poupardin, O.; Greck, C.; Genet, J.-P. Tetrahedron Lett. 2000, 41, 8795.
27. (b) Dolls, D. A.; Vanhessche, K. P. M.; Brazi, E.; Rautenstrauch, V.; Lenoir, J.-Y.; Genet, J.-P.; Wiles, J.; Bergens, S. H. Angew. Chem. Int. Ed. 2000, 39, 1992.
28. (a) Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
29. (b) Review: Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
30. (c) Review. Ratovelomanana-Vidal, V.; Genet, J.-P. Can. J. Chem. 2000, 78, 846.
31. (a) Genet, J.-P.; Pinel, C.; Mallart, S.; Juge, S.; Thorimbert, S.; Laffitte, J. A. Tetrahedron: Asymmetry 1991, 2, 555.
32. (b) Girard, A.; Greck, C.; Ferroud, D.; Genet, J.-P. Tetrahedron Lett. 1996, 37, 7967.
33. (c) Coulon, E.; Cano de Andrade, M. C.; Ratovelomanana-Vidal, V.; Genet, J.-P. Tetrahedron Lett. 1998, 39, 6467.
34. (d) Phansavath, P.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genet, J.-P. Eur. J. Org. Chem. 2000, 3903.
35. Genet, J.-P.; Pfister, X.; Ratovelomanana-Vidal, V.; Pinel, C.; Laffitte, J. A. Tetrahedron Lett. 1994, 35, 4559.
36. Lavergne, D.; Mordant, C.; Ratovelomanana-Vidal, V.; Genet, J.-P. Org. Lett. 2001, 3, 1909.
37. (a) Sayo, N.; Sano, N.; Kumobayachi, H. Takasago, European Patent 0519763 A2,1992.
38. (b) Genet, J.-P.; Cano de Andrade, M. C.; Ratovelomanana-Vidal, V. Tetrahedron Lett. 1995, 36, 2063.
39. The choice of the configuration of the ligand follows the general sense of the asymmetric induction: Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
40. Genet, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño de Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665.