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Asymmetric Reduction of Acetophenones with NaBH4 in the Presence of Mono-6-(1-methyl-3-imidazolium)-6-deoxy-β-cyclodextrin tosylate

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An Erratum to this article was published on 10 May 2006

Abstract

The asymmetric reduction of acetophenone and its derivatives was achieved with sodium borohydride utilizing a novel chiral ionic liquid of β-cylclodextrin (CD), mono-6-(1-methyl-3-imidazolium)-6-deoxy-β-cyclodextrin tosylate (MIM-β-CDOTs). It was found that this chiral β-CD-based ionic liquid could provide higher enantioselectivity for the product alcohols. Moreover, the enantioselectivity of the product alcohols was highly dependent on the structure of prochiral ketones, structure of CD and reduction temperature.

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References

  1. Howarth J., Hanlon K., Mccormac P., (1997) Tetrahedron Lett. 38:3097

    Article  CAS  Google Scholar 

  2. Ishida Y., Miyauchi H., Saigo K., (2002) Chem. Commun. 19:2240

    Article  CAS  Google Scholar 

  3. Yanes E.G., Gratz S.R., Baldwin M.J., Robinson S.E., Stalcup A.M., (2001) Anal. Chem. 73:3838

    Article  PubMed  CAS  Google Scholar 

  4. Anderson J.L., Armstrong D.W., (2003) Anal. Chem. 75: 4851

    Article  PubMed  CAS  Google Scholar 

  5. Armstrong D.W., He L.F., Liu Y.S., (1999) Anal. Chem. 71: 3873

    Article  PubMed  CAS  Google Scholar 

  6. Yanes E.G., Gratz S.R., Stalcup A.M., (2000) Analyst 125: 1919

    Article  PubMed  CAS  Google Scholar 

  7. Earle M.J., McCormac P.B., Seddon K.R., (1999) Green Chem. 1: 23

    Article  CAS  Google Scholar 

  8. Wasserscheid P., Bösmann A., Bolm C., (2002) Chem. Commun. 3: 200

    Article  CAS  Google Scholar 

  9. Takahashi K., (1998) Chem. Rev. 98: 2013

    Article  PubMed  CAS  Google Scholar 

  10. Reddy L.R., Bhanumathi N., Rao K.R., (2000) Chem. Commun. 20:2321

    Article  Google Scholar 

  11. R. Fornasier, F. Reniero, P. Scrimin, and U. Tonellato: J. Org. Chem. 50, 3209 (1985); (b) K.K. Park, W.-J. Sim, and J.W. Park: J.␣Incl. Phenom. Mol. Recog. Chem. 27, 41 (1997); (c) A. Deratani and E. Renard: Chirality 6, 658 (1994)

  12. A. Schlatter, M.K. Kundu, and W.-D. Woggon: Angew. Chem. Int. Ed. 43, 6731 (2004); (b) M.A. Reddy, N. Bhanumathi, and K.R. Rao: Chem. Commun. 19, 1974 (2001); (c) Y. Kawajiri and N. Motohashi: J. Chem. Soc., Chem. Commun. 1336 (1989); (d) T. Maraldo and A. Deratani: Minutes of the fifth International Symposium on Cyclodextrins, Paris, 659 (1990)

  13. F. Toda and T. Shigemasa: Carbohydr. Res. 192, 363 (1989); (b) W.-S. Chung, N.J. Turro, J. Silver, and W.J. Le Noble: J. Am. Chem. Soc. 112, 1202 (1990); (c) G. Mehta, F.A. Khan, and K.A. Lakshmi: Tetrahedron Lett. 33, 7977 (1992)

  14. Easton C.J., Lincoln S.F., (1996) Chem. Soc. Rev. 25:163

    Article  CAS  Google Scholar 

  15. Muderawan I.W., Ong T.-T., Tang W.-H., Young D.J., Ching C.-B., Ng S.-C., (2005) Tetrahedron Lett. 46:1747

    Article  CAS  Google Scholar 

  16. W.-H. Tang, T.-T. Ong, and S.-C. Ng: Electrophoresis 26, 3125 (2005)

    Google Scholar 

  17. W.-H. Tang, I.W. Muderawan, T.-T. Ong, and S.-C. Ng: Anal. Chim. Acta 546, 119 (2005)

    Google Scholar 

  18. Lai X.-H., Ng S.-C., (2003) Tetrahedron Lett. 44:2657

    Article  CAS  Google Scholar 

  19. U. Nagai, T. Shishido, R. Chiba, and H. Mitsuhashi: Tetrahedron 21, 1701 (1965); (b) H.M.D. Peters, M.H. Feigl, and S. Mosher: J.␣Org. Chem. 33, 4245 (1968); (c) J. Buckingham (ed.), Dictionary of Organic Compounds, Vol. 5, (5th edn), Chapman and Hall, New York (1982) p. 4609

  20. Liu L., Guo Q.-X., (2002) J. Incl. Phenom. Mol. Recog. Chem. 42:1

    Article  CAS  Google Scholar 

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Acknowledgements

Financial support for this work was provided by the National University of Singapore (NUS) and Institute of Chemical and Engineering Sciences, Singapore. Weihua Tang also acknowledges the NUS for awarding the research scholarship.

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Authors and Affiliations

  1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore

    Weihua Tang, Jian Tang & Hardy Sze On Chan

  2. Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, 50 Nanyang Avenue, 639798, Singapore, Singapore

    Siu-Choon Ng

Authors
  1. Weihua Tang
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  2. Jian Tang
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  3. Siu-Choon Ng
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  4. Hardy Sze On Chan
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Corresponding author

Correspondence to Hardy Sze On Chan.

Additional information

An erratum to this article can be found at http://dx.doi.org/10.1007/s10847-005-9037-2

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Tang, W., Tang, J., Ng, SC. et al. Asymmetric Reduction of Acetophenones with NaBH4 in the Presence of Mono-6-(1-methyl-3-imidazolium)-6-deoxy-β-cyclodextrin tosylate. J Incl Phenom Macrocycl Chem 56, 287–290 (2006). https://doi.org/10.1007/s10847-005-9018-5

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  • DOI: https://doi.org/10.1007/s10847-005-9018-5

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