Resolution of α-methylene-β-hydroxy esters catalyzed by free and immobilized Pseudomonas sp. lipase

Tetrahedron Asymmetry

Volumn 14, Issue 20, 2003, Pages 3111-3115

  Nascimento, M G ^a   Zanotto, Sandra P ^a   Melegari, Sílvia P ^a   Fernandes, Luciano ^a   Sá, Marcus Mandolesi ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; BACTERIAL ENZYME; HEXANE; HYDROXYL GROUP; MACROGOL; MONTMORILLONITE; SILICA GEL; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYST; ENANTIOSELECTIVITY; ENZYME IMMOBILIZATION; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS; TRANSESTERIFICATION;

EID: 1642331561     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.015     Document Type: Article

References (40)

1. Roush W.R., Brown B.B. J. Org. Chem. 58:1993;2151-2161.
2. Iwabuchi Y., Furukawa M., Esumi T., Hatakeyama S. J. Chem. Soc., Chem. Commun. 2001;2030-2031.
3. Bailey M., Markó I.E., Ollis W.D., Rasmussen P.R. Tetrahedron Lett. 31:1990;4509-4512.
4. Ameer F., Drewes S.E., Hoole R., Kaye P.T., Pitchford A.T. J. Chem. Soc., Perkin Trans. 1. 1985;2713-2717.
5. Hoffmann H.M.R., Rabe J. J. Org. Chem. 50:1985;3849-3859.
6. Hoffmann H.M.R., Rabe J. Helv. Chim. Acta. 2:1984;413-415.
7. Cheskis B.A., Moiseenkov A.M., Shpiro N.A., Stashina G.A., Zhulin V.M. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.). 39:1990;716-720.
8. Moiseenkov A.M., Cheskis B.A., Shpiro N.A., Stashina G.A., Zhulin V.M. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.). 39:1990;517-521.
9. Mateus C.R., Feltrin M.P., Costa A.M., Coelho F., Almeida W.P. Tetrahedron. 57:2001;6901-6908.
10. Kim J.N., Chung Y.M., Im Y.J. Tetrahedron Lett. 43:2002;6209-6211.
11. Annunziata R., Benaglia M., Cinquini M., Cozzi F., Raimondi L. J. Org. Chem. 60:1995;4697-4706.
12. Räcker R., Döring K., Reiser O. J. Org. Chem. 65:2000;6932-6939.
13. Basavaiah D., Kumaragurubaran N. Tetrahedron Lett. 42:2001;477-479.
14. Kundu M.K., Sundar N., Kumar S.K., Bhat S.V., Biswas S., Valecha N. Bioorg. Med. Chem. Lett. 9:1999;731-736.
15. Basavaiah D., Rao A.J., Satyanarayana T. Chem. Rev. 103:2003;811-891.
16. Basavaiah D., Rao P.D., Hyma R.S. Tetrahedron. 52:1996;8001-8062.
17. Ciganek E. Organic Reactions. 51:1997;201-350 John Wiley & Sons, New York.
18. Drewes S.E., Roos G.H.P. Tetrahedron. 44:1988;4653-4670.
19. Langer P. Angew. Chem., Int. Ed. 39:2000;3049-3052.
20. Brzezinsky L.J., Rafel S., Leahy J.W. J. Am. Chem. Soc. 119:1997;4317-4318.
21. Yang K.-S., Chen K. Org. Lett. 2:2000;729-731.
22. Krishna P.R., Kannan V., Ilangovan A., Sharma G.V.M. Tetrahedron: Asymmetry. 12:2001;829-837.
23. Iwabuchi Y., Nakatani M., Yokoyama N., Hatakeyama S. J. Am. Chem. Soc. 121:1999;10219-10220.
24. Trost B.M., Tsui H.-C., Toste F.D. J. Am. Chem. Soc. 122:2000;3534-3535.
25. Kitamura M., Kasahara I., Manabe K., Noyori R. J. Org. Chem. 53:1988;708-710.
26. Brown J.M. Angew. Chem., Int. Ed. Engl. 26:1987;190-203.
27. Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1:1999;1-21.
28. Roberts S.M. Biocatalysis for Fine Chemical Synthesis. 1999;John Wiley & Sons, New York.
29. Yang H., Henke E., Bornscheur U.T. J. Org. Chem. 64:1999;1709-1712.
30. Kobayashi S., Uyama H., Namekawa S., Hayakawa H. Macromolecules. 1998;5655-5659.
31. Al-Azemi T.F., Bisht K.S. Macromolecules. 1998;6536-6540.
32. Morisso F.D.P., Costa V.E.U. Tetrahedron: Asymmetry. 12:2001;2641-2647.
33. Queiroz N., Nascimento M.G. Tetrahedron Lett. 43:2002;5225-5227.
34. Adam W., Hoch U., Saha-Möller C.R., Schreier P. Angew. Chem., Int. Ed. Engl. 32:1993;1737-1739.
35. Basavaiah D., Rao P.D. Synth. Commun. 24:1994;913-917.
36. Burgess K., Jennings L.D. J. Org. Chem. 55:1990;1138-1139.
37. Hayashi N., Yanagihara K., Tsuboi S. Tetrahedron: Asymmetry. 9:1998;3825-3830.
38. Sih C.J., Wu S.-H. Top. Stereochem. 19:1989;63-125.
39. 22.
40. Pleiss J., Fischer M., Schimidt R.D. Chem. Phys. Lipids. 93:1998;67-80.