Lipase-catalyzed remote kinetic resolution of arylic nitriles with adjacent quaternary chiral center and the determination of their absolute configuration

Journal of Molecular Catalysis B: Enzymatic

Volumn 26, Issue 3-6, 2003, Pages 131-143

  Im, Dai Sig ^b   Cheong, Chan Seong ^a   Lee, So Ha ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Comp Aided Molec Des/Biosci R ^*  (South Korea)

Author keywords

Arylic nitrile; Biocatalyst; Lipase; Resolution

Indexed keywords

ALCOHOLS; ENZYME KINETICS; MICROORGANISMS;

CHEMICAL TRANSFORMATIONS;

ENZYMES;

2 (4 CHLOROPHENYL) 2 CYANO 2 PHENYL 1 HEXANOL; 2 CYANO 2 (3,4 DIMETHOXYPHENYL) 3 METHYL 1 BUTANOL; 2 CYANO 2 (4 CHLOROPHENYL) 1 HEXANOL; 2 CYANO 2 PHENYL 1 PROPANOL; 3 (4 CHLOROPHENYL) 3 CYANO 1 HEPTANOL; 3 CYANO 3 (3,4 DIMETHOXYPHENYL) 4 METHYL 1 PENTANOL; 3 CYANO 3 PHENYL 1 HEPTANOL; 4 CYANO 4 PHENYL 1 PENTANOL; ALCOHOL DERIVATIVE; NITRILE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA RUGOSA; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHIRALITY; ENZYME MECHANISM; PSEUDOMONAS FLUORESCENS; QUATERNARY; SYNTHESIS; TRANSESTERIFICATION;

BURKHOLDERIA CEPACIA; CANDIDA; CANDIDA RUGOSA; PSEUDOMONAS; PSEUDOMONAS FLUORESCENS;

EID: 0242490883     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2003.05.002     Document Type: Article

References (26)

1. (a) Corey E.J., Guzmn-Perez A. Angew. Chem. Int. Ed. Engl. 37:1998;388
2. (b) Fuji K. Chem. Rev. 93:1993;2037
3. (c) Nartin S.F. Tetrahedron. 36:1980;419
4. (d) Seebach D., Sting A.R. Angew. Chem. Int. Ed. Engl. 35:1996;2708.
5. Convery M.A., Davis A.P., Dunne C.J., Mackinnon J.W. Tetrahedron Lett. 36:1995;4279.
6. Tiecco M., Testaferri L., Tingoli M., Bartoli D. Tetrahedron. 45:1989;6819.
7. Trivedi B.K., Holmes A., Stoeber T.L., Blankley C.J., Roark W.H., Picard T.A., Shaw M.K., Essenburg A.D., Stanfield R.L., Krause B.R. J. Med. Chem. 36:1993;3300.
8. Wenkert E., Buckwalter B.L., Crareiro A.A., Sancher E.L., Sathe S.S. J. Am. Chem. Soc. 100:1978;1267.
9. (a) Im D.S., Cheong C.S., Lee S.H., Park H., Youn B.H. Tetrahedron: Asymmetry. 10:1999;3759
10. (b) Holland H.L., Gu J.-X., Orallo F., Camina M., Fabeiro P., Willetts A. J. Pharm. Res. 16:1999;281.
11. (b) Quinn J.A., Fujimoto T.T., Egan A.R., Shaber S.H. Pestic. Sci. 17:1986;357
12. (b) Ruano J.L.G., Castro M.C.A.M.M., Ramos J.H.R. Org. Lett. 55:2002;55.
13. (a) R.N. Patel, Stereoselective Biocatalysis, Marcel Dekker, New York, 2000
14. (b) K. Drauz, H. Waldmann, Enzymatic Catalysis in Organic Synthesis, 2nd ed., Wiley-VCH, Weinheim, 2002
15. (c) S.M. Robert, J. Chem. Soc., Perkin I (2001) 1475.
16. Norimine Y., Yamamoto N., Suzuki Y., Kimura T., Kawano K., Ito K., Nagato S., Limura Y., Yonaga M. Tetrahedron: Asymmetry. 13:2002;1493.
17. Stanek J., Alder A., Bellus D., Bhatnager A.S., Hausler A., Schieweck K. J. Med. Chem. 4:1991;1329.
18. Leader H., Smejkal R.M., Payne C.S., Padilla F.N., Doctor B.P., Gordon R.K., Chiang P.K. J. Med. Chem. 32:1989;1522.
19. Okatani T., Koyama J., Tagahara K. Heterocycles. 29:1989;1809.
20. Frohlick J., Sauter F., Blasl K. Heterocycles. 37:1994;1879.
21. Im D.S., Cheong C.S., Lee S.H., Youn B.H., Kim S.C. Tetrahedron. 56:2000;1309.
22. (a) Nicolaou K.C., Petasis N.A., Uenishi J., Zipkin R.E. J. Am. Chem. Soc. 104:1982;5557
23. (b) Knabe J., Junginger H., Geismar W. Arch. Pharm. 303:1970;705.
24. Theodore L.J., Nelson W.L. J. Org. Chem. 52:1987;1309.
25. Chen C.-S., Fujimoto Y., Girdaukas G., Sih C. J. Am. Chem. Soc. 104:1982;7294.
26. Bushell S.M., Crump J.P., Lawence N.J., Pineau G. Tetrahedron. 54:1998;2269.