Kinetic resolution of racemic 2-substituted 3-cyclopenten-1-ols by lipase-catalyzed transesterifications: A rational strategy to improve enantioselectivity

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8610-8616

  Ema, Tadashi ^a   Maeno, Soichi ^a   Takaya, Yusuke ^a   Sakai, Takashi ^a   Utaka, Masanori ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANOL DERIVATIVE; CYCLOPENTANE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; DRUG PURIFICATION; ENANTIOMER; ENZYME ACTIVITY; TECHNIQUE;

EID: 0029969716     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961144s     Document Type: Article

References (65)

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35. For the effect of the chain length of acyl donors on the enantioselectivity in the lipase-catalyzed acylations using enol esters, see: (a) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. (b) Hiratake, J.; Inagaki, M.; Nishioka, T.; Oda, J. J. Org. Chem. 1988, 53, 6130. (c) Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. Agric. Biol. Chem. 1989, 53, 1879. (d) Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4942. (e) Yamazaki, Y.; Hosono, K. Tetrahedron Lett. 1990, 31, 3895. (f) Miyazawa, T.; Kurita, S.; Ueji, S.; Yamada, T.; Kuwata, S. J. Chem. Soc., Perkin Trans. 1 1992, 18, 2253. (g) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (h) Tokuyama, S.; Yamano, T.; Aoki, I.; Takanohashi, K.; Nakahama, K. Chem. Lett. 1993, 741.
36. For the effect of the chain length of acyl donors on the enantioselectivity in the lipase-catalyzed acylations using enol esters, see: (a) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. (b) Hiratake, J.; Inagaki, M.; Nishioka, T.; Oda, J. J. Org. Chem. 1988, 53, 6130. (c) Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. Agric. Biol. Chem. 1989, 53, 1879. (d) Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4942. (e) Yamazaki, Y.; Hosono, K. Tetrahedron Lett. 1990, 31, 3895. (f) Miyazawa, T.; Kurita, S.; Ueji, S.; Yamada, T.; Kuwata, S. J. Chem. Soc., Perkin Trans. 1 1992, 18, 2253. (g) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (h) Tokuyama, S.; Yamano, T.; Aoki, I.; Takanohashi, K.; Nakahama, K. Chem. Lett. 1993, 741.
37. For the effect of the chain length of acyl donors on the enantioselectivity in the lipase-catalyzed acylations using enol esters, see: (a) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. (b) Hiratake, J.; Inagaki, M.; Nishioka, T.; Oda, J. J. Org. Chem. 1988, 53, 6130. (c) Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. Agric. Biol. Chem. 1989, 53, 1879. (d) Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4942. (e) Yamazaki, Y.; Hosono, K. Tetrahedron Lett. 1990, 31, 3895. (f) Miyazawa, T.; Kurita, S.; Ueji, S.; Yamada, T.; Kuwata, S. J. Chem. Soc., Perkin Trans. 1 1992, 18, 2253. (g) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (h) Tokuyama, S.; Yamano, T.; Aoki, I.; Takanohashi, K.; Nakahama, K. Chem. Lett. 1993, 741.
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40. For the effect of the chain length of acyl donors on the enantioselectivity in the lipase-catalyzed acylations using the acyl donors other than enol esters, see: (a) Sonnet, P. E. J. Org. Chem. 1987, 52, 3477. (b) Stokes, T. M.; Oehlschlager, A. C. Tetrahedron Lett. 1987, 28, 2091. (e) Okahata, Y.; Fujimoto, Y.; Tjiro, K. Tetrahedron Lett. 1988, 29, 5133. Holmberg, E.; Szmulik, P.; Norin, T.; Hult, K. Biocatalysis 1989, 2, 217. (e) Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4942.
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54. The acylation with vinyl trifluoroacetate in the absence of the lipase did proceed, and small amounts of trifluoroacetic acid generated in situ seemed to induce the lactonization of 1 during the reaction; isolated yield of 2 27% (13% ee for (1S,5R)-form).
55. 5.
56. 21 indicating that the stereochemistry is governed primarily by the size and shape of the binding pocket of the lipase.
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59. It should be noted here that the present strategy is quite different from the enzymatic hydrolysis of racemic esters in water, where ester derivatives of a racemic alcohol with various acyl groups are examined; e.g. Ehrler, J.; Seebach, D. Liebigs Ann. Chem. 1990, 379. By changing the solvent from water to organic solvents, attractive interactions such as hydrophobic interaction change to another types of interactions such as steric repulsion. Such transition of the intermolecular force will change the thermodynamic stability of the intermediates, and hence can potentially lead to a drastically altered enantioselectivity as compared with the reaction in water.
60. This tactics was also found to be effective for the kinetic resolution of other types of racemic alcohols such as linear aliphatic alcohol.
61. The parameter P represents the partition coefficient of a solvent between 1-octanol and water. (a) Leo, A.; Hansch, C.; Elkins. D. Chem. Rev. 1971, 71, 525. (b) Laane, C.; Boeren, S.; Vos, K.; Veeger, C. Biotechnol. Bioeng. 1987, 30, 81.
62. The parameter P represents the partition coefficient of a solvent between 1-octanol and water. (a) Leo, A.; Hansch, C.; Elkins. D. Chem. Rev. 1971, 71, 525. (b) Laane, C.; Boeren, S.; Vos, K.; Veeger, C. Biotechnol. Bioeng. 1987, 30, 81.
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