Horse liver esterase catalyzed enantioselective hydrolysis of N,O- diacetyl-2-amino-1-arylethanol

Tetrahedron Asymmetry

Volumn 9, Issue 1, 1998, Pages 169-178

  Laïb, Taoues ^a   Ouazzani, Jamal ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; N,O DIACETYL 2 AMINO 1 ARYLETHANOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME MECHANISM; HYDROLYSIS; PRIORITY JOURNAL;

EID: 0032536061     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00610-1     Document Type: Article

References (44)

1. Dictionary of Drugs, Elks, J.; Ganellin, C. R. (Eds), Chapman and Hall, 1990, p. 1160.
2. ibid, 358.
3. (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69;
4. (b) Ajer, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
5. For some selected examples, see: (a) Elliott, J. D.; Choi, V. M. F.; Johnson, W. S. J. Org. Chem. 1983, 48, 2294-2295;
6. (b) Yamashita, H. Chem. Lett. 1987, 525-528;
7. (c) Kitamura, M.; Okhuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H. Noyori, R. J. Am. Chem. Soc. 1988, 110, 629-631;
8. (d) Ziegler, T.; Hörsch, B.; Effenberger, F. Synthesis 1990, 575-578;
9. (e) Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442-444;
10. (f) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546;
11. (g) Oppolzer, W.; Tamura, O.; Sundarababu, G.; Signer, M. J. Am. Chem. Soc. 1992, 114, 5900-5904;
12. (h) An, B.; Kim, H.; Cha, J. K. J. Org. Chem. 1993, 58, 1273-1275;
13. (i) Kawaguchi, T.; Saito, K.; Matsuki, K.; Iwakuma, T.; Takeda, M. Chem. Pharm. Bull. Jpn 1994, 41, 639-642;
14. (j) Donohue, A. C.; Jackson, W. R. Aust. J. Chem. 1995, 48, 1741-1746;
15. (k) Li, G.; Chang, H. T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454;
16. (l) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421;
17. (m) Effenberger, F.; Jäger, J. J. Org. Chem. 1997, 62, 3867-3873 and references cited therein.
18. Zhu, J.; Laib, T.; Chastanet, J.; Beugelmans, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2517-2519.
19. North, M. Synlett 1993, 807-820.
20. Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1564.
21. (a) Matthews, B. R.; Jackson, W. R.; Jayatilake, G. S.; Wilshire, C.; Jacobs, H. A. Aust. J. Chem. 1988, 41, 1697-1709;
22. (b) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans 1 1997, 1293-1295.
23. Faber, K. Biotransformation In Organic Chemistry, Springer-Verlag, 2nd Edn, 1995, pp. 240-243.
24. Vergne, C.; Bois-Choussy, M.; Ouazzani, J.; Beugelmans, R.; Zhu, J. Tetrahedron: Asymmetry 1997, 8, 391-398.
25. (a) Francalanci, F.; Cesti, P.; Cabri, W.; Bianchi, D.; Martinengo, T.; Foa, M. J. Org. Chem. 1987, 52, 5079-5082;
26. (b) Gotor, V.; Brieva, R.; Rebolledo, F. J. Chem. Soc., Chem. Commun. 1988, 957-958;
27. (c) Bevinakatti, H. S.; Newadkar, R. V. Tetrahedron: Asymmetry 1990, 1, 583-586;
28. (d) Nieduzak, T. R.; Carr, A. A.; Tetrahedron: Asymmetry 1990, 1, 535-536;
29. (e) Ader, U.; Schneider, M. P. Tetrahedron: Asymmetry 1992, 3, 205-208;
30. (f) Fernandez, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1992, 2885-2889;
31. (g) Maestro A.; Astorga, C.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 3153-3159 and references cited therein.
32. (a) Kanerva, L. T.; Rahiala, K.; Vänttinen, E. J. Chem. Soc., Perkin Trans. 1 1992, 1759-1762;
33. (b) Izumi, T.; Fukaya, K. Bull. Chem. Soc. Jpn 1993, 66, 1216-1221;
34. (c) Lundell, K.; Kanerva, L. T. Tetrahedron: Asymmetry 1995, 6, 2281-2286;
35. (d) Takayama, S.; Moree, W. J.; Wong, C. H. Tetrahedron Lett. 1996, 37, 6287-6290.
36. Evans, D. A.; Carroll, G. L.; Truesdale, L. K. J. Org. Chem. 1974, 39, 914-917.
37. Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Kilbanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094-3095;
38. (b) Sakurai, T.; Margolin, A. L.; Russel, A. J.; Kilbanov, A. M. J. Am. Chem. Soc. 1988, 110, 7236-7237.
39. Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396.
40. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519;
41. (b) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147;
42. (c) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
43. Steric crowding around the ester moiety may cause the irregularity, see: (a) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Org. Chem. 1991, 56, 1296-1298;
44. (b) Kusumi, T.; Fujita, Y.; Ohtani, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2923-2926. However, in our case, steric hinderance is not obvious. We think that the possible intramolecular hydrogen bond between the amide proton and the ester carbonyl function may modify the MTPA plane and cause this observed irregularity.