Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Lipase-catalyzed Remote Kinetic Resolution of Quaternary Carbon-containing Alcohols and Determination of Their Absolute Configuration

  • Im, Dai-Sig (Computer-aided Molecular Design & Bioscience Research Co., Ltd.) ;
  • Cheong, Chan-Seong (Life Science Divistion, Korea Insitute of Science and Technology) ;
  • Lee, So-Ha (Life Science Divistion, Korea Insitute of Science and Technology)
  • Published : 2003.09.20
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Abstract

The quaternary carbon-containing alcohols (1-6) were resolved enantioselectively by various lipases such as PFL (Pseudomonas fluorescens lipase), LAK (Pseudomonas fluorescens lipase), CRL (Candida rugosa lipase) and PCL (Pseudomonas cepacia lipase). The enzymatic resolution of racemic alcohol $({\pm})-2$ gave the excellent enantioselectivity in favor of (S)-2d in 99% ee, while those of the racemic alcohols (1, 3, 4, 5 and 6) gave the resolved alcohols with moderate to good enantioselectivity. Also, their absolute configurations were determined by chemical transformation to the known compounds.

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References

  1. Pogorevc, M.; Faber, K. J. Mol. Cat. B: Enzymatic 2000, 10,357. https://doi.org/10.1016/S1381-1177(99)00121-6
  2. Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit, S. Tetrahedron Lett. 1981, 22, 4107. https://doi.org/10.1016/S0040-4039(01)82078-5
  3. Caron, S.; Vazquez, E.;Wojcik, J. M. J. Am. Chem. Soc. 2000, 122, 712. https://doi.org/10.1021/ja9933846
  4. Zoltewicz, J.A. Top. Curr. Chem. 1975, 59, 33. https://doi.org/10.1007/BFb0046186
  5. Carnell, A. J.; Hernandez, M. L. E.; Pettman, A.; Bickley, J. F.Tetrahedron Lett. 2000, 41, 6929. https://doi.org/10.1016/S0040-4039(00)01149-7
  6. Soine, W. H. Med. Res. Rev. 1986, 6, 41. https://doi.org/10.1002/med.2610060103
  7. Fadel, A.; Garcia-Argote, S. Tetrahedron: Asymmetry 1996, 7,1159. https://doi.org/10.1016/0957-4166(96)00122-X
  8. Im, D. S.; Cheong, C. S.; Lee, S. H.; Park, H.; Youn, B. H.Tetrahedron: Asymmetry 1999, 10, 3759. https://doi.org/10.1016/S0957-4166(99)00389-4
  9. Im, D. S.; Cheong, C. S.; Lee, S. H.; Youn, B. H.; Kim, S. C.Tetrahedron 2000, 56, 1309. https://doi.org/10.1016/S0040-4020(00)00031-4
  10. Weber, H. K.; Stecher, H.; Faber, K. Biotech. Lett. 1995. 17,803. https://doi.org/10.1007/BF00129008
  11. Khmelnitsky, Y. L.; Welch, S. H.; Clark, D. S.; Dordick, J.S. J. Am Chem. Soc. 1994, 116, 2647. https://doi.org/10.1021/ja00085a066
  12. Itoh, T.; Takagi, Y.;Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61,2158. https://doi.org/10.1021/jo951598+
  13. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. Am. Chem.Soc. 1982, 104, 7294. https://doi.org/10.1021/ja00389a064
  14. Kroutil, W.; Kleewein, A.; Faber, K. Tetrahedron: Asymmetry1997, 8, 3251. https://doi.org/10.1016/S0957-4166(97)00428-X
  15. Hartmann, R. W.; Batzl, C. J. Med. Chem. 1986, 29, 1362. https://doi.org/10.1021/jm00158a007
  16. Ruano, J. L. G.; Garcia, M. C.; Castro, A. M. M.; Ramos, J. H. R.Org. Lett. 2002, 4, 55. https://doi.org/10.1021/ol0168723

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