Lipase-catalyzed kinetic resolution of 7-, 8- and 12-membered alicyclic β-amino esters and N-hydroxymethyl-β-lactam enantiomers

Tetrahedron Asymmetry

Volumn 14, Issue 23, 2003, Pages 3805-3814

  Gyarmati, Zsuzsanna Cs ^a,b   Liljeblad, Arto ^a   Rintola, Mikko ^a   Bernáth, Gábor ^b   Kanerva, Liisa T ^a  

^a UNIVERSITY OF TURKU   (Finland)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

13 HYDROXYMETHYL 13 AZABICYCLO[10.2.0]TETRADECAN 14 ONE; 8 HYDROXYMETHYL 8 AZABICYCLO[5.5.0]NONAN 9 ONE; 9 HYDROXYMETHYL 9 AZABICYCLO[6.2.0]DECAN 10 ONE; ACETONE; ACID LIPASE; BETA LACTAM DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; KETONE DERIVATIVE; LIPASE B; METHYL 2 AMINOCYCLOCTANECARBOXYLATE; METHYL 2 AMINOCYCLODODECANECARBOXYLATE; METHYL 2 AMINOCYCLOHEPTANECARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA; CATALYSIS; CATALYST; ENANTIOMER; ENZYME KINETICS; NONHUMAN; OPTICAL RESOLUTION; PRIORITY JOURNAL;

EID: 0344585370     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.028     Document Type: Article

References (32)

1. Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VHC: New York, 1997.
2. Gademann K., Hintermann T., Schreiber J.V. Curr. Med. Chem. 6:1999;905-925.
3. Ojima I., Lin S., Wang T. Curr. Med. Chem. 6:1999;927-954.
4. Scarborough R.M. Curr. Med. Chem. 6:1999;971-981.
5. Fülöp F. Chem. Rev. 101:2001;2181-2204.
6. Park K., Kurth M.J. Tetrahedron. 58:2002;8629-8659.
7. Nativ E., Rona P. Isr. J. Chem. 10:1972;55-58.
8. Rasmussen J.K., Hassner A. Chem. Rev. 76:1976;389-408.
9. Singh R., Cooper R.D.G. Tetrahedron. 50:1994;12049-12064.
10. Csomós P., Kanerva L.T., Bernáth G., Fülöp F. Tetrahedron: Asymmetry. 7:1996;1789-1796.
11. Kámán J., Forró E., Fülöp F. Tetrahedron: Asymmetry. 11:2000;1593-1600.
12. Fülöp F., Palkó M., Kámán J., Lázár L., Sillanpää R. Tetrahedron: Asymmetry. 11:2000;4179-4187.
13. Forró E., Árva J., Fülöp F. Tetrahedron: Asymmetry. 12:2001;643-649.
14. Forró E., Fülöp F. Org. Lett. 5:2003;1209-1212.
15. Martinek T.M., Tóth G.K., Vass E., Hollósi M., Fülöp F. Angew. Chem., Int. Ed. 41:2002;1718-1721.
16. Oki T., Hirano M., Tomatsu K., Numata K., Kamei H. J. Antibiot. 42:1989;1756-1762.
17. Iwamato T., Tsujii E., Ezaki M., Fujie A., Hashimoto S., Okuhara M., Kohsaka M., Imanaka H., Kawabata K., Inamato Y., Sakane K. J. Antibiot. 43:1990;1-7.
18. Kanerva L.T., Csomós P., Sundholm O., Bernáth G., Fülöp F. Tetrahedron: Asymmetry. 7:1996;1705-1716.
19. Evans C., McCague R., Roberts S.M., Sutherland A.G., Wisdom R. J. Chem. Soc., Perkin Trans. 1. 1991;2276-2277.
20. Taylor S.J.M., McCague R., Wisdom R., Lee C., Dickson K., Ruecroft G., O'Brien F., Littlechild J., Bevan J., Roberts S.M., Evans C.T. Tetrahedron: Asymmetry. 4:1993;1117-1128.
21. Halling P.J. Enzyme Microb. Technol. 16:1994;178-206.
22. Liljeblad A., Kanerva L.T. Tetrahedron: Asymmetry. 10:1999;4405-4415.
23. Virsu P., Liljeblad A., Kanerva A., Kanerva L.T. Tetrahedron: Asymmetry. 12:2001;2447-2455.
24. Paizs C., Tosa M., Majdik C., Tähtinen P., Irimie F.D., Kanerva L.T. Tetrahedron: Asymmetry. 14:2003;619-627.
25. Gedey S., Liljeblad A., Lázár L., Fülöp F., Kanerva L.T. Tetrahedron: Asymmetry. 12:2001;105-110.
26. Solymar M., Fülöp F., Kanerva L.T. Tetrahedron: Asymmetry. 13:2002;2383-2388.
27. Liljeblad A., Lindborg J., Kanerva A., Katajisto J., Kanerva L.T. Tetrahedron Lett. 43:2002;2471-2474.
28. Liljeblad, A.; Kiviniemi, A.; Kanerva, L. T. Tetrahedron: Asymmetry 2003, 44, in press.
29. Högberg H.-E., Lindmark M., Isaksson D., Sjödin K., Franssen M.C.R., Jongejan H., Wijnberg J.B.P.A., de Groot A. Tetrahedron Lett. 41:2000;3193-3196.
30. Bornscheuer U.T., Kazlauskas R.J. Hydrolysis in Organic Synthesis, Regio- and Stereoselective Biotransformations. 1999;Wiley-VHC, Weinheim.
31. Kanerva L.T., Sundholm O. J. Chem. Soc., Perkin Trans. 1. 1993;2407-2410.
32. Chen C.-S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294-7299.