Enantiospecific synthesis of dihydropyridines from chiral enamines

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 1985-1994

  Caballero, Esther ^a   Puebla, Pilar ^a   Sánchez, Mar ^a   Medarde, Manuel ^a   Morán Del Prado, Lourdes ^a,b   San Feliciano, Arturo ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b UNIVERSITY OF HAVANA   (Cuba)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030200771     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00239-X     Document Type: Article

References (29)

1. 1.-Bossert, F.; Meyer, H. and Wehinger, E. Angew. Chem. Int. Ed. Engl. 1981, 20, 762. Janis, R.A. and Triggle, D.J. J. Med. Chem. 1983, 26, 775.
2. 1.-Bossert, F.; Meyer, H. and Wehinger, E. Angew. Chem. Int. Ed. Engl. 1981, 20, 762. Janis, R.A. and Triggle, D.J. J. Med. Chem. 1983, 26, 775.
3. 2.-Bossert, F. and Vater, W. Med. Res. Rev. 1989, 9, 291.
4. 3.-Rampe, D. and Triggle, D.J. Prog. Drug Res. 1993, 40, 191. Rovnyak, G.C.; Kimball, S.D.; Beyer, B.; Cucinotta, G.; DiMarco, J.D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J.P.; Zhang, R. and Moreland, S. J. Med. Chem. 1995, 38, 119.
5. 3.-Rampe, D. and Triggle, D.J. Prog. Drug Res. 1993, 40, 191. Rovnyak, G.C.; Kimball, S.D.; Beyer, B.; Cucinotta, G.; DiMarco, J.D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J.P.; Zhang, R. and Moreland, S. J. Med. Chem. 1995, 38, 119.
6. 4.-Goldmann, S. and Stoltefuss, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 1559.
7. 5.-Alajarin, R.; Alvarez-Builla, J.; Vaquero, J.J.; Sunkel, C; Fau de Casa-Juana, M.; Statkow, P.R. and Sanz-Aparicio, J. Tetrahedron Asymm. 1993, 4, 617. Satoh, Y.; Okamura, K. and Shikowa, Y. Chem. Pharm. Bull. 1994, 42, 950. Wester, R.T.; Mularski, Ch.J.; Magnus-Ayriety, J.T.; Da Silva Jardine, P.; LaFlamme, J.A.; Berke, H.; Bussolotti, D.L.; Rauch, A.L.; Hoover, K.W.; Kennedy, Ch.A.; Burkard, M.R.; Mangiapane, M.L.; Aldinger, Ch.E.; Cooper, K. and Carpino. Ph.A. BioMed. Chem. Lett. 1994, 4, 133. Ogawa, T.; Matsumoto, K.; Yokoo, C.; Hatayama, K. and Kitamura, K. J. Chem. Soc. Perkin Trans. 1 1993, 525.
8. 5.-Alajarin, R.; Alvarez-Builla, J.; Vaquero, J.J.; Sunkel, C; Fau de Casa-Juana, M.; Statkow, P.R. and Sanz-Aparicio, J. Tetrahedron Asymm. 1993, 4, 617. Satoh, Y.; Okamura, K. and Shikowa, Y. Chem. Pharm. Bull. 1994, 42, 950. Wester, R.T.; Mularski, Ch.J.; Magnus-Ayriety, J.T.; Da Silva Jardine, P.; LaFlamme, J.A.; Berke, H.; Bussolotti, D.L.; Rauch, A.L.; Hoover, K.W.; Kennedy, Ch.A.; Burkard, M.R.; Mangiapane, M.L.; Aldinger, Ch.E.; Cooper, K. and Carpino. Ph.A. BioMed. Chem. Lett. 1994, 4, 133. Ogawa, T.; Matsumoto, K.; Yokoo, C.; Hatayama, K. and Kitamura, K. J. Chem. Soc. Perkin Trans. 1 1993, 525.
9. 5.-Alajarin, R.; Alvarez-Builla, J.; Vaquero, J.J.; Sunkel, C; Fau de Casa-Juana, M.; Statkow, P.R. and Sanz-Aparicio, J. Tetrahedron Asymm. 1993, 4, 617. Satoh, Y.; Okamura, K. and Shikowa, Y. Chem. Pharm. Bull. 1994, 42, 950. Wester, R.T.; Mularski, Ch.J.; Magnus-Ayriety, J.T.; Da Silva Jardine, P.; LaFlamme, J.A.; Berke, H.; Bussolotti, D.L.; Rauch, A.L.; Hoover, K.W.; Kennedy, Ch.A.; Burkard, M.R.; Mangiapane, M.L.; Aldinger, Ch.E.; Cooper, K. and Carpino. Ph.A. BioMed. Chem. Lett. 1994, 4, 133. Ogawa, T.; Matsumoto, K.; Yokoo, C.; Hatayama, K. and Kitamura, K. J. Chem. Soc. Perkin Trans. 1 1993, 525.
10. 5.-Alajarin, R.; Alvarez-Builla, J.; Vaquero, J.J.; Sunkel, C; Fau de Casa-Juana, M.; Statkow, P.R. and Sanz-Aparicio, J. Tetrahedron Asymm. 1993, 4, 617. Satoh, Y.; Okamura, K. and Shikowa, Y. Chem. Pharm. Bull. 1994, 42, 950. Wester, R.T.; Mularski, Ch.J.; Magnus-Ayriety, J.T.; Da Silva Jardine, P.; LaFlamme, J.A.; Berke, H.; Bussolotti, D.L.; Rauch, A.L.; Hoover, K.W.; Kennedy, Ch.A.; Burkard, M.R.; Mangiapane, M.L.; Aldinger, Ch.E.; Cooper, K. and Carpino. Ph.A. BioMed. Chem. Lett. 1994, 4, 133. Ogawa, T.; Matsumoto, K.; Yokoo, C.; Hatayama, K. and Kitamura, K. J. Chem. Soc. Perkin Trans. 1 1993, 525.
11. 6.-Ebiike, H. and Achiwa, K. Tetrahedron Asymm. 1994, 5, 1447. Hirose, Y.; Kariya, K.; Nakanishi, Y.; Kurono, Y. and Achiwa, K. Tetrahedron Lett. 1995, 36, 1063. Yamazaki, Y.; Ebiike, H. and Achiwa, K. Chem. Pharm. Bull. 1994, 42, 1968.
12. 6.-Ebiike, H. and Achiwa, K. Tetrahedron Asymm. 1994, 5, 1447. Hirose, Y.; Kariya, K.; Nakanishi, Y.; Kurono, Y. and Achiwa, K. Tetrahedron Lett. 1995, 36, 1063. Yamazaki, Y.; Ebiike, H. and Achiwa, K. Chem. Pharm. Bull. 1994, 42, 1968.
13. 6.-Ebiike, H. and Achiwa, K. Tetrahedron Asymm. 1994, 5, 1447. Hirose, Y.; Kariya, K.; Nakanishi, Y.; Kurono, Y. and Achiwa, K. Tetrahedron Lett. 1995, 36, 1063. Yamazaki, Y.; Ebiike, H. and Achiwa, K. Chem. Pharm. Bull. 1994, 42, 1968.
14. 7.-Davis, R.; Kern, J.R.; Kurz, L.J. and Pfister, J.R. J. Am. Chem. Soc. 1988, 110, 7973. Arrowsmith, J.E.; Campbell, S.F.; Cross, P.E.; Stubbs, J.K.; Burges, R.A.; Gardiner, D.G. and Blackburn, K.J. J. Med. Chem. 1986, 29, 1696.
15. 7.-Davis, R.; Kern, J.R.; Kurz, L.J. and Pfister, J.R. J. Am. Chem. Soc. 1988, 110, 7973. Arrowsmith, J.E.; Campbell, S.F.; Cross, P.E.; Stubbs, J.K.; Burges, R.A.; Gardiner, D.G. and Blackburn, K.J. J. Med. Chem. 1986, 29, 1696.
16. 8.-Hof, R.P.; Ruegg, U.T.; Hof, A. and Vogel, A. J. Cardiovasc. Pharmacol. 1985, 7, 689. Goldmann, S. and Stoltefuss, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 1559. Rovnyak, G.C.: Kimball, S.D.; Beyer, B.; Cucinotta, G.; DiMarco, J.D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J.P.; Zhang, R. and Moreland, S. J. Med. Chem. 1995, 38, 119.
17. 8.-Hof, R.P.; Ruegg, U.T.; Hof, A. and Vogel, A. J. Cardiovasc. Pharmacol. 1985, 7, 689. Goldmann, S. and Stoltefuss, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 1559. Rovnyak, G.C.: Kimball, S.D.; Beyer, B.; Cucinotta, G.; DiMarco, J.D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J.P.; Zhang, R. and Moreland, S. J. Med. Chem. 1995, 38, 119.
18. 8.-Hof, R.P.; Ruegg, U.T.; Hof, A. and Vogel, A. J. Cardiovasc. Pharmacol. 1985, 7, 689. Goldmann, S. and Stoltefuss, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 1559. Rovnyak, G.C.: Kimball, S.D.; Beyer, B.; Cucinotta, G.; DiMarco, J.D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J.P.; Zhang, R. and Moreland, S. J. Med. Chem. 1995, 38, 119.
19. 9.-Enders, D.; Müller, S. and Demir A.S. Tetrahedron Lett. 1988, 29, 6437.
20. 10.-Kosugi, Y.; Hori, M. and Nagasaka, T. Heterocycles 1994, 39, 591.
21. 11.-Caballero, M.; Puebla, P.; Medarde, M.; Sánchez, M.; Salvadó, M.A.; García-Granda, S. and San Feliciano, A. J. Org. Chem. 1996, 61, 1890.
22. 12.-Bonadies, F.; Di Fabio, R. J. Org. Chem. 1984, 49, 1647.
23. 13.-Taber, D. F.; Schuchardt, J. L. J. Am. Chem. Soc. 1985, 107, 5289.
24. 14.-Li, J. H.; Snyder, J. K. Tetrahedron Lett. 1994, 35, 1485. Schmidt, H. J.; Schafer, H. J. Angew. Chem. Int. Ed. Eng. 1981, 20, 109.
25. 14.-Li, J. H.; Snyder, J. K. Tetrahedron Lett. 1994, 35, 1485. Schmidt, H. J.; Schafer, H. J. Angew. Chem. Int. Ed. Eng. 1981, 20, 109.
26. 15.-Schmidt, H. J.; Schafer, H. J. Angew. Chem. Int. Ed. Eng. 1979, 18, 69.
27. 16.-San Feliciano, A.; Caballero, E.; Pereira, J.A.P.; Puebla, P. Tetrahedron, 1991, 47, 6503. Caballero, E.; Puebla, P.; Medarde, M.; San Feliciano, A. Tetrahedron 1993, 49, 10079.
28. 16.-San Feliciano, A.; Caballero, E.; Pereira, J.A.P.; Puebla, P. Tetrahedron, 1991, 47, 6503. Caballero, E.; Puebla, P.; Medarde, M.; San Feliciano, A. Tetrahedron 1993, 49, 10079.
29. 17.-McKillop, A.; Boulton, A. J. in Comprehensive Heterocyclic Chemistry., Katritzky A. R., Rees C. V. Eds. Pergamon Press. Oxford, 1984.Vol. 2, p. 482.