Chemoenzymatic preparation of optically active trans-cyclohexane-1,2- diamine derivatives: An efficient synthesis of the analgesic U-(-)-50,488

Chemistry - A European Journal

Volumn 10, Issue 22, 2004, Pages 5788-5794

  González Sabín, Javier ^a   Gotor, Vicente ^a   Rebolledo, Francisca ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Asymmetric synthesis; Chemoenzymatic synthesis; Diamines; Kinetic resolution; Lipases

Indexed keywords

CATALYSTS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMINOLYSIS; DONORS; KINETIC RESOLUTIONS; PRECURSORS;

AMINES;

3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; ACETAMIDE DERIVATIVE; ACETIC ACID ETHYL ESTER; ALKYL GROUP; AMMONIA; ANALGESIC AGENT; AZIRIDINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CYCLOHEXANOL DERIVATIVE; CYCLOHEXENE DERIVATIVE; DIAMINE DERIVATIVE; LIPASE B; SOLVENT;

AMINOLYSIS; ARTICLE; CANDIDA ANTARCTICA; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; ENZYME MECHANISM; OPTICAL ROTATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

3,4-DICHLORO-N-METHYL-N-(2-(1-PYRROLIDINYL)-CYCLOHEXYL)-BENZENEACETAMIDE, (TRANS)-ISOMER; AMINES; ANALGESICS; CYCLOHEXANES; DIAMINES; ENZYMES, IMMOBILIZED; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RECEPTORS, OPIOID, KAPPA; STEREOISOMERISM;

EID: 9244231110     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400607     Document Type: Article

References (38)

1. For some reviews, see: a) F. Fache, E. Schulz, M. L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231;
2. b) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627;
3. b) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627;
4. c) Y. L. Bennani, S. Hanessian, Chem. Rev. 1997, 97, 3161-3195.
5. For some recent applications, see: d) T. Olszewska, M. Gdaniec, T. Po-lonski, J. Org. Chem. 2004, 69, 1248-1255;
6. e) E. M. McGarrigle, D. M. Murphy, D. G. Gilheany, Tetrahedron: Asymmetry 2004, 15, 1343-1354;
7. f) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11204-11205.
8. E. T. Michalson, J. Szmuszkovicz, Prog. Drug Res. 1989, 33, 135-149.
9. J. Szmuszkovicz, P. F. Von Voigtlander, J. Med. Chem. 1982, 25, 1125-1126.
10. a) J. Szmuszkovicz, EP 126612, 1984; [Chem. Abstr. 1985, 102, 184969b];
11. b) C. R. Clark, P. R. Halfpenny, R. G. Hill, D. C. Horwell, J. Hughes, T. C. Jarvis, D. C. Rees, D. Schofield, J. Med. Chem. 1988, 31, 831-836;
12. c) G. F. Costello, R. James, J. S. Shaw, A.M. Slater, N. C. J. Stutchbury, J. Med. Chem. 1991, 34, 181-189;
13. d) J. J. Barlow, T. P. Blackburn, G. F. Costello, R. James, D. J. Le Count, B. G. Main, R. J. Pearce, K. Russell, J. S. Shaw, J. Med. Chem. 1991, 34, 3149-3158.
14. a) A. Cowan, D. E. Gmerek, Trends Pharmacol. Sci. 1986. 7, 69-72;
15. b) M. J. Millan, Trends Pharmacol Sci. 1990, 11, 70-76.
16. a) B. R. De Costa, W. D. Bowen, S. B. Hellewell, C. George, R. B. Rothman, A. A. Reid, J. M. Walker, A. E. Jacobson, K. C. Rice, J. Med. Chem. 1989, 32, 1996-2002;
17. b) B. R. De Costa, W. D. Bowen, A. Thurkauf, D. T. Finn, S. Vazirani, R. B. Rothman, L. Band, P. C. Contreras, N. M. Gray, J. Med. Chem. 1990, 33, 3100-3110.
18. a) S. Hanessian, D. Delorme, S. Beaudoin, Y. Leblanc, J. Am. Chem. Soc. 1984, 106, 5754-5756;
19. b) A. Alexakis, S. Mutti, P. Mangeney, J. Org. Chem. 1992, 57, 1224-1237;
20. c) Y. L. Bennani, S. Hanessian, Tetrahedron 1996, 52, 13837-13866;
21. A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178.
22. M. Kaik, J. Gawronski, Tetrahedron: Asymmetry 2003, 14, 1559-1563, and references therein.
23. a) P. O'Brien, P. Poumellec, Tetrahedron Lett. 1996, 37, 5619-5622;
24. b) E. Curthbertson, P. O'Brien, T. D. Towers, Synthesis 2001, 693-695.
25. a) M. Mousseron, J. Jullien, Y. Jolchine, Bull. Soc. Chim. Fr. 1952, 19, 757-766;
26. b) J. González-Sabín, V. Gotor, F. Rebolledo, Tetrahedron: Asymmetry 2004, 15, 1335-1341.
27. For some applications of aziridinium ions in synthesis, see: a) M. Couturier, J. L. Tucker, B. M. Andresen, K. M. DeVries, B. C. Vanderplas, F. Ito, Tetrahedron: Asymmetry 2003, 14, 3517-3523;
28. b) D. G. Piotrowska, A. E. Wroblewski, Tetrahedron 2003, 59, 8405-8410;
29. c) D. R. Andrews, V. H. Dahanukar, J. M. Eckert, D. Gala, B. S. Lucas, D. P. Schumacher, I. A. Zavialov, Tetrahedron Lett. 2002, 43, 6121-6125;
30. d) T.-H. Chuang, K. B. Sharpless, Org. Lett. 2000, 2, 3555-3557.
31. For some recent reviews, see: a) F. Van Rantwijk, R. A. Sheldon, Tetrahedron 2004, 60, 501-519;
32. b) I. Alfonso, V. Gotor, Chem. Soc. Rev. 2004, 53, 201-209;
33. c) E. M. Anderson, K. M. Larsson, O. Kirk, Biocatal. Biotransform. 1998, 16, 181-204.
34. a) I. Alfonso, C. Astorga, F. Rebolledo, V. Gotor, Chem. Commun. 1996, 2471-2472;
35. b) I. Alfonso, F. Rebolledo, V. Gotor, Chem. Eur. J. 2000, 6, 3331-3338.
36. C. S. Chen, Y. Fujimoto, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299.
37. B. De Costa, C. George, R. B. Rothman, A. E. Jacobson, K. C. Rice, FEBS Lett. 1987, 223, 335-339.
38. R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656-2665.