Optical resolution of (±)-1-aryl-1-alkanols using enantioselective transesterification by lipases

Enantiomer

Volumn 5, Issue 1, 2000, Pages 63-70

  Negi, Shigeru ^a   Umetsu, Kazunori ^a   Nishijo, Yoshiteru ^a   Kano, Koji ^a   Nakamura, Kaoru ^b  

^a DOSHISHA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

1 Aryl 1 alkanols; Enantioselective transesterification; Lipases; Optical resolution; Pseudomonas aeruginosa (LIP)

Indexed keywords

1 ARYL 1 ALKANOL; ALKANOL; ALKYL GROUP; BACTERIAL ENZYME; BENZENE; PROPANOL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VINYL ACETATE; ALCOHOL DERIVATIVE; AROMATIC HYDROCARBON; BACTERIAL PROTEIN; ESTER; FUNGAL PROTEIN;

ARTICLE; DRUG ISOLATION; ENANTIOMER; ENZYME SPECIFICITY; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL RESOLUTION; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STEREOCHEMISTRY; BURKHOLDERIA CEPACIA; CANDIDA; CATALYSIS; CHEMISTRY; COMPARATIVE STUDY; ENZYMOLOGY; METABOLISM; OPTICAL ROTATION; PSEUDOMONAS FLUORESCENS; RHIZOMUCOR; STEREOISOMERISM;

ALCOHOLS; BACTERIAL PROTEINS; BURKHOLDERIA CEPACIA; CANDIDA; CATALYSIS; ESTERIFICATION; ESTERS; FUNGAL PROTEINS; HYDROCARBONS, AROMATIC; LIPASE; OPTICAL ROTATION; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS FLUORESCENS; RHIZOMUCOR; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0033624856     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. (a) G.M. Whiteside and C.-H. Wong, Angew. Chem. Int. Ed. Engl., 1985, 24, 617;
2. (b) K. Drauz and H. Waldmann (Eds.), Enzyme Catalysis in Organic Synthesis, Weinheim, 1995;
3. (c) K. Faber, Biotransformations in Organic Chemistry, Springer, 1995;
4. (d) A.M.P. Koskinen and A.M. Klibanov (Eds.), Enzymatic Reactions in Organic Media, Chapman & Hall, Glasgow, 1996.
5. (a) A.M. Klibanov, Ace. Chem. Res., 1990, 23, 114;
6. (b) W. Boland, C. Frößl and M. Lorenz, Synthesis, 1991, 1049;
7. (c) K. Faber and S. Riva, Synthesis, 1992, 895.
8. (a) T. Ohtani, H. Nakatsukasa, M. Kamezawa, H. Tachibana and Y. Naoshima, J. Mol. Catal. B, 1998, 4, 53;
9. (b) M. Cygler, P. Grochulski, R.J. Kazlauskas, J.D. Schrag, F. Bouthillier, B. Rubin, A.N. Serreqi and A.K. Gupta, J. Am. Chem. Soc., 1994, 116, 3180;
10. (c) B. Morgan, A.C. Oehlschlager and T.M. Stokes, J. Org. Chem., 1992, 57, 3231.
11. K. Kano, S. Negi, A. Kawashima and K. Nakamura, Enantiomer, 1997, 2, 261.
12. I. Petschen, E.A. Malo, M.P. Bosch and A. Guerrero, Tetrahedron: Asymmetry, 1996, 7, 2135.
13. (a) K. Nakamura, M. Kawasaki and A. Ohno, A. Bull. Chem. Soc. Jpn., 1996, 69, 1079;
14. (b) K. Naemura, R. Fukuda, M. Konishi, K. Hirose and Y. Tobe, J. Chem. Soc., Perkin Trans. 1, 1994, 1253;
15. (c) K. Naemura, M. Murata, R. Tanaka, M. Yano, K. Hirose and Y. Tobe, Tetrahedron: Asymmetry, 1996, 7, 1581;
16. (d) P. Ferraboschi, S. Casati, A. Manzocchi and E. Santaniello, Tetrahedron: Asymmetry, 1995, 6, 1521.
17. J.G. Rodriguez and Y. Benito, J. Heterocycl. Chem. 1988, 25, 819.
18. In Dictionary of Organic Compounds. Fifth edn, Chapman & Hall, London, 1982-1983.
19. C. Lutz and P. Knochel, J. Org. Chem., 1997, 62, 7695.
20. D. Seeback, H.-O. Kalinowiski, B. Batani, G. Crass, H. Daum, H. Dörr, N.P. Dupreez, V. Ehrig, W. Langer, C. Nüssler, H.-A. Oei and M. Schmidt, Helv. Chim. Acta, 1977, 60, 301.
21. B.M. Trost, J.L. Belletire, S. Godleski, P.G. McDougal, J.M. Balkovec, J.J. Baldwin, M.E. Christy, G.S. Ponticello, S.L. Varga and J.P. Springer, J. Org. Chem., 1986, 51, 2370.
22. A. Hassner and V. Alexanian, Tetrahedron Lett., 1978, 4475.
23. J.A. Dale and H.S. Mosher, J. Am. Chem. Soc., 1973, 95, 512.
24. (a) T. Ema, M. Jittani, T. Sakai and M. Utaka, Tetrahedron Lett., 1998, 6311;
25. (b) K. Kato, M. Katayama, S. Fujii and H. Kimoto, Biosci. Biotech. Biochem., 1995, 59, 2178;
26. (c) M. Uemura, H. Nishimura, S. Yamada, K. Hayashi, K. Nakamura, K. Ishihara and A. Ohno, Tetrahedron: Asymmetry, 1994, 5, 1673;
27. (d) M. Inagaki, J. Hiratake, T. Nishioka and J. Oda, Agric. Biol. Chem., 1989, 57(7), 1879.
28. (a) R.J. Kazlauskas, A.N.E. Weissfloch, A. Rappaport and L.A. Cuccia, J. Org. Chem., 1991, 56, 2656.
29. M. Arroyo and J.V. Sinisterra, J. Org. Chem., 1994, 59, 4410.
30. M.J. Garcia, F. Rebolledo and V. Gotor, Tetrahedron: Asymmetry, 1992, 3, 1519.
31. C.-S. Chen, Y. Fujimoto, G. Girdaukas and C.J. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
32. G. Kirchner, M.P. Scollar and A.M. Klibanov, J. Am. Chem. Soc., 1985, 107, 7072.
33. K.-H. Engel, Tetrahedron: Asymmetry, 1991, 2, 165.
34. T. Miyazawa, S. Kurita, S. Shinichi, T. Yamada and S. Kuwata, J. Chem. Soc. Perkin Trans. 1, 1992, 2253.
35. S. Parida and J.S. Dordick, J. Org. Chem., 1993, 53, 3238.
36. S. Parida and J.S. Dordick, J. Am. Chem. Soc., 1991, 113, 2253.
37. T. Ema, J. Kobayashi, S. Maeno, T. Sakai and M. Utaka, Bull. Chem. Soc. Jpn., 1998, 71, 443.