Improvement of enantioselectivity in kinetic resolution of a primary alcohol through lipase-catalyzed transesterification by using a chiral acyl donor

Tetrahedron Asymmetry

Volumn 11, Issue 5, 1999, Pages 1199-1210

  Hirose, Keiji ^a   Naka, Hiroyuki ^a   Yano, Masashi ^a   Ohashi, Sozaburo ^a   Naemura, Koichiro ^a   Tobe, Yoshito ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLPROPANOL; ACYL DONOR; ALCOHOL; HYDROXYL GROUP; SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VINYL 3 PHENYLBUTANOATE;

ARTICLE; CATALYSIS; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; ESTERIFICATION; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0343130518     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00060-4     Document Type: Article

References (36)

1. Crout, D. H. G.; Chrisen, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, pp. 1-114. Davies, H. G.; Green, R. H.; Kelly, D. R.; Roberts, S. M. Biotransformation in Preparative Organic Chemistry; Academic Press: London, 1990. Wong, C. H.; Whitesides, G. W. Enzymes in Synthetic Organic Chemistry. Tetrahedron Organic Chemistry Series; Pergamon: Oxford, 1994; Vol. 12. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Naemura, K.; Kittaka, K.; Murata, M.; Ida, H.; Hirose, K.; Tobe, Y. Enantiomer 1996, 1, 219.
2. Crout, D. H. G.; Chrisen, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, pp. 1-114. Davies, H. G.; Green, R. H.; Kelly, D. R.; Roberts, S. M. Biotransformation in Preparative Organic Chemistry; Academic Press: London, 1990. Wong, C. H.; Whitesides, G. W. Enzymes in Synthetic Organic Chemistry. Tetrahedron Organic Chemistry Series; Pergamon: Oxford, 1994; Vol. 12. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Naemura, K.; Kittaka, K.; Murata, M.; Ida, H.; Hirose, K.; Tobe, Y. Enantiomer 1996, 1, 219.
3. Crout, D. H. G.; Chrisen, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, pp. 1-114. Davies, H. G.; Green, R. H.; Kelly, D. R.; Roberts, S. M. Biotransformation in Preparative Organic Chemistry; Academic Press: London, 1990. Wong, C. H.; Whitesides, G. W. Enzymes in Synthetic Organic Chemistry. Tetrahedron Organic Chemistry Series; Pergamon: Oxford, 1994; Vol. 12. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Naemura, K.; Kittaka, K.; Murata, M.; Ida, H.; Hirose, K.; Tobe, Y. Enantiomer 1996, 1, 219.
4. Crout, D. H. G.; Chrisen, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, pp. 1-114. Davies, H. G.; Green, R. H.; Kelly, D. R.; Roberts, S. M. Biotransformation in Preparative Organic Chemistry; Academic Press: London, 1990. Wong, C. H.; Whitesides, G. W. Enzymes in Synthetic Organic Chemistry. Tetrahedron Organic Chemistry Series; Pergamon: Oxford, 1994; Vol. 12. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Naemura, K.; Kittaka, K.; Murata, M.; Ida, H.; Hirose, K.; Tobe, Y. Enantiomer 1996, 1, 219.
5. Crout, D. H. G.; Chrisen, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, pp. 1-114. Davies, H. G.; Green, R. H.; Kelly, D. R.; Roberts, S. M. Biotransformation in Preparative Organic Chemistry; Academic Press: London, 1990. Wong, C. H.; Whitesides, G. W. Enzymes in Synthetic Organic Chemistry. Tetrahedron Organic Chemistry Series; Pergamon: Oxford, 1994; Vol. 12. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Naemura, K.; Kittaka, K.; Murata, M.; Ida, H.; Hirose, K.; Tobe, Y. Enantiomer 1996, 1, 219.
6. Kazlauskas, R. J.; Weissfloch, A. M. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656. Naemura, K.; Fukuda, R.; Konishi, M.; Hirose, K.; Tobe, Y. J. Chem. Soc., Perkin Trans. 1 1994, 1253. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Tuomi, W. V.; Kazlauskas, R. J. J. Org. Chem. 1999, 64, 2638.
7. Kazlauskas, R. J.; Weissfloch, A. M. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656. Naemura, K.; Fukuda, R.; Konishi, M.; Hirose, K.; Tobe, Y. J. Chem. Soc., Perkin Trans. 1 1994, 1253. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Tuomi, W. V.; Kazlauskas, R. J. J. Org. Chem. 1999, 64, 2638.
8. Kazlauskas, R. J.; Weissfloch, A. M. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656. Naemura, K.; Fukuda, R.; Konishi, M.; Hirose, K.; Tobe, Y. J. Chem. Soc., Perkin Trans. 1 1994, 1253. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Tuomi, W. V.; Kazlauskas, R. J. J. Org. Chem. 1999, 64, 2638.
9. Kazlauskas, R. J.; Weissfloch, A. M. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656. Naemura, K.; Fukuda, R.; Konishi, M.; Hirose, K.; Tobe, Y. J. Chem. Soc., Perkin Trans. 1 1994, 1253. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385. Tuomi, W. V.; Kazlauskas, R. J. J. Org. Chem. 1999, 64, 2638.
10. Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1. Koskinen, A. M. P. Enzymatic Reactions in Organic Media; Klibanov, A. M., Ed.; Blackie Academic: Glasgow, 1996. Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366. Tanaka, K.; Yasuda, M. Tetrahedron: Asymmetry 1998, 9, 3275.
11. Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1. Koskinen, A. M. P. Enzymatic Reactions in Organic Media; Klibanov, A. M., Ed.; Blackie Academic: Glasgow, 1996. Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366. Tanaka, K.; Yasuda, M. Tetrahedron: Asymmetry 1998, 9, 3275.
12. Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1. Koskinen, A. M. P. Enzymatic Reactions in Organic Media; Klibanov, A. M., Ed.; Blackie Academic: Glasgow, 1996. Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366. Tanaka, K.; Yasuda, M. Tetrahedron: Asymmetry 1998, 9, 3275.
13. Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1. Koskinen, A. M. P. Enzymatic Reactions in Organic Media; Klibanov, A. M., Ed.; Blackie Academic: Glasgow, 1996. Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366. Tanaka, K.; Yasuda, M. Tetrahedron: Asymmetry 1998, 9, 3275.
14. Sakai, T.; Kishimoto, T.; Tanaka, Y.; Ema, T.; Utaka, M. Tetrahedron Lett. 1998, 39, 7881. Sakai, T.; Kawabata, I.; Kishimoto, T.; Ema, T.; Utaka, M. J. Org. Chem. 1997, 62, 4906.
15. Sakai, T.; Kishimoto, T.; Tanaka, Y.; Ema, T.; Utaka, M. Tetrahedron Lett. 1998, 39, 7881. Sakai, T.; Kawabata, I.; Kishimoto, T.; Ema, T.; Utaka, M. J. Org. Chem. 1997, 62, 4906.
16. Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6836. Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617. Itoh, T.; Mitsukura, K.; Kanphai, W.; Takagi, Y.; Kihara, H.; Tsukube, H. J. Org. Chem. 1997, 62, 9165.
17. Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6836. Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617. Itoh, T.; Mitsukura, K.; Kanphai, W.; Takagi, Y.; Kihara, H.; Tsukube, H. J. Org. Chem. 1997, 62, 9165.
18. Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6836. Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617. Itoh, T.; Mitsukura, K.; Kanphai, W.; Takagi, Y.; Kihara, H.; Tsukube, H. J. Org. Chem. 1997, 62, 9165.
19. Lin, G.; Lin, W.-Y. Tetrahedron Lett. 1998, 39, 4333.
20. Berger, B.; Faber, K. J. Chem. Soc., Chem. Commun. 1991, 1198.
21. Hirose, Y.; Kiriya, K.; Nakanishi, Y.; Kurono, Y.; Achiwa, K.; Tetrahedron Lett. 1995, 36, 1063.
22. Berglund, P.; Holmquist, M.; Hult, K.; Hogberg, H. E. Biotechnology Lett. 1995, 17, 55. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610.
23. Berglund, P.; Holmquist, M.; Hult, K.; Hogberg, H. E. Biotechnology Lett. 1995, 17, 55. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610.
24. Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610.
25. The E values for the reactions using isopropenyl acetate and methyl 3-phenylpropanoate are 2 and 6, respectively. The procedures of each reaction are the same as those of entry 10 described in the Experimental section using isopropenyl acetate or methyl 3-phenylpropanoate as an acyl donor.
26. Kawasaki, M.; Goto, M.; Kawabata, S.; Kodama, T.; Kometani, T. Tetrahedron Lett. 1999, 10, 5223.
27. As examples of the use of chiral acyl donors: for the resolution of chiral secondary alcohol and secondary chiral amine, see: Pozo, M.; Gotor, V. Tetrahedron: Asymmetry 1995, 6, 2797; for hydrolysis catalyzed by Candisa rugosa lipase, see: Berglund, P.; Holmquist, M.; Hult, K. J. Mol. Catalysis B-Enzymatic 1998, 5, 283.
28. As examples of the use of chiral acyl donors: for the resolution of chiral secondary alcohol and secondary chiral amine, see: Pozo, M.; Gotor, V. Tetrahedron: Asymmetry 1995, 6, 2797; for hydrolysis catalyzed by Candisa rugosa lipase, see: Berglund, P.; Holmquist, M.; Hult, K. J. Mol. Catalysis B-Enzymatic 1998, 5, 283.
29. Naemura, K.; Murata, M.; Tanaka, R.; Yano, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1996, 7, 3285.
30. Yamamoto, K.; Ikeda, K.; Yin, L. K. J. Organomet. Chem. 1989, 370, 319.
31. Swern, D.; Billen, G. N.; Knight, H. B. J. Am. Chem. Soc. 1947, 69, 2439.
32. Levene, P. A.; Rothen, A. J. Org. Chem. 1936, 1, 76. Jaouen, G.; Meyer, A. J. Am. Chem. Soc. 1975, 97, 466.
33. Levene, P. A.; Rothen, A. J. Org. Chem. 1936, 1, 76. Jaouen, G.; Meyer, A. J. Am. Chem. Soc. 1975, 97, 466.
34. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. Am. Chem. Soc. 1982, 104, 7294.
35. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129.
36. Hæffner, F.; Norin, T. Chem. Pharm. Bull. 1999, 47, 591.