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Synthesis and kinetic resolution of furyl substituted secondary carbinols by porcine pancreatic lipase under solvent free conditions

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Abstract

Chiral furyl substituted carbinols were prepared from the related carbonyl compounds and their enzymatic kinetic resolution was studied by using porcine pancreatic lipase (PPL) in transesterification reaction under solvent free condition. This study revealed that carbinols having one less bulky group on the chiral center are good substrates for PPL and the resolution proceeds with higher ee,s and less reaction time.

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References

  1. A. Ghanem, H.Y. Aboul-Enein, Tetrahedron: Asymmetry 15 (2004) 3331.

    CAS  Google Scholar 

  2. F. Theil, Chem. Rev. 95 (1995) 2203.

    CAS  Google Scholar 

  3. K. Faber, Pure Appl. Chem. 69 (1997) 1613.

    CAS  Google Scholar 

  4. T. Itoh, Y. Takagi, H. Tsukube, J. Mol. Catal. B: Enzym. 3 (1997) 259.

    CAS  Google Scholar 

  5. R.D. Scmid, R. Veger, Angew. Chem., Int. Ed. Engl. 37 (1998) 1609.

    Google Scholar 

  6. C. Tanyeli, E. Turkut, Tetrahedron: Asymmetry 15 (2004) 2057.

    CAS  Google Scholar 

  7. A. Liljeblad, L.T. Kanerva, Tetrahedron 62 (2006) 5831.

    CAS  Google Scholar 

  8. E. Garcia-Urdiales, L. Alfonso, V. Gotor, Chem. Rev. 105 (2005) 313.

    CAS  Google Scholar 

  9. K. Faber, Biotransformation in Organic Chemistry, 3rd, inger, Heidelberg 1997.

    Google Scholar 

  10. E. Santaniello, P. Ferraboschi, A. Manzocchi, Chem. Rev. 92 (1992) 1071.

    CAS  Google Scholar 

  11. B.G. Davis, V. Boyer, Nat. Prod. Rep. 18 (2001) 618.

    CAS  Google Scholar 

  12. A. Bierstedt, J. Stolting, R. Frohlich, P. Metz, Tetrahedron: Asymmetry 12 (2001) 3399.

    Google Scholar 

  13. O. Achmatowicz, in: B.M. Trost, C.R. Hutchinson (Eds.), Organic Synthesis Today and Tomorrow, Pergamon Press, 1981, pp. 307-318.

  14. A. Zamojski, G. Grynkiewicz, in: J. Simon (Ed.), The Total Synthesis of Natural Products, Wiley, New York, 1984, pp.141–235.

    Google Scholar 

  15. C. Held, R. Frohlich, P. Metz, Angew. Chem., Int. Ed. Engl. 40 (2001) 1058.

    CAS  Google Scholar 

  16. M. Mamaghani, K. Tabatabaeian, A. Ghanadzadeh, F. Habibi, Tetrahedron Lett. 44 (2003) 4775

    CAS  Google Scholar 

  17. M.Mamaghani, K. Tabatabaeian, B. Bahrami, J. Chem.Res. (2003) 256

  18. M. Mamaghani, Tetrahedron 58(2002) 147

    CAS  Google Scholar 

  19. M. Mamaghani, A. Alizadeh, J. Chem.Res. (2002) 386

    Google Scholar 

  20. M. Mamaghani, J.H. Klunder, B. Zwanenburg, J. Sci. I.R. Iran 11 (2000) 205

    CAS  Google Scholar 

  21. M. Mamaghani, A. Namazi, J. Sci. I.R. Iran 10 (1999) 169.

    CAS  Google Scholar 

  22. K. Kaminska, L. Gornicka, M. Sikora, J. Gora, Tetrahedron Lett. 12 (2000) 907.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, The University of Guilan, P.O. Box 41335-1914, Rasht, Iran

    M. Mamaghani, N. O. Mahmoodi, A. A. Moghisseh & L. Pourmohamad

Authors
  1. M. Mamaghani
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  2. N. O. Mahmoodi
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  3. A. A. Moghisseh
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  4. L. Pourmohamad
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Correspondence to M. Mamaghani.

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Mamaghani, M., Mahmoodi, N.O., Moghisseh, A.A. et al. Synthesis and kinetic resolution of furyl substituted secondary carbinols by porcine pancreatic lipase under solvent free conditions. JICS 5, 238–243 (2008). https://doi.org/10.1007/BF03246113

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  • DOI: https://doi.org/10.1007/BF03246113

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