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Chemical Research in Chinese Universities

, Volume 33, Issue 5, pp 742–745 | Cite as

Synthesis of a newly modified poly-H8-BINOL ligand and its applications in the asymmetric addition of triethylaluminium to aromatic aldehydes

Article

Abstract

A new H8-BINOL polymer was synthesized by radical polymerization and proved to be an effective catalyst in enantioselective addition of triethylaluminium to aromatic aldehydes in the presence of titanium isopropoxide. The polymer can be prepared with simple steps and reused without losing its enantioselectivity and catalytic activity.

Keywords

H8-BINOL Radical polymerization Triethylaluminium Asymmetric addition Enantioselectivity 

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Supplementary material

40242_2017_7093_MOESM1_ESM.pdf (1003 kb)
Synthesis of a newly modified poly-H8-BINOL ligand and its applications in the asymmetric addition of triethylaluminium to aromatic aldehydes

References

  1. [1]
    Brunel J. M., Chem. Rev., 2005, 105, 4233CrossRefGoogle Scholar
  2. [2]
    Chan A. S. C., Zhang F. Y., Yip C. W., J. Am. Chem. Soc., 1997, 119, 4080CrossRefGoogle Scholar
  3. [3]
    Cram D. J., Helgeson R. C., Peacock S. C., Kaplan L. J., Domeier L. A., Moreau P., K., Koga J. Mayer M., Chao Y., J. Org. Chem., 1978, 43, 1930CrossRefGoogle Scholar
  4. [4]
    Wang B., Feng X., Huang Y., Liu H., Cui X., Jiang Y., J. Org. Chem., 2002, 67, 2175CrossRefGoogle Scholar
  5. [5]
    Zhang F. Y., Yip C. W., Cao R., Chan A. S. C., Tetrahedron Asymme-try, 1997, 8, 585CrossRefGoogle Scholar
  6. [6]
    Zhang F. Y., Chan A. S. C., Tetrahedron Asymmetry, 1997, 8, 3651CrossRefGoogle Scholar
  7. [7]
    Reetz M. T., Merk C., Naberfeld G., Rudolph J., Griebenow N., Goddard R., Tetrahedron Lett., 1997, 38, 5273CrossRefGoogle Scholar
  8. [8]
    Long J., Hu J., Shen X., Ji B., Ding K., J. Am. Chem. Soc., 2002, 124, 10CrossRefGoogle Scholar
  9. [9]
    Waltz K. M., And P. J. C., Walsh P. J., Organometallics, 2003, 23, 127CrossRefGoogle Scholar
  10. [10]
    Au-Yeung T. T. L., Chan S. S., Chan A. S. C., Adv. Synth. Catal., 2003, 345, 537CrossRefGoogle Scholar
  11. [11]
    Zhang F. Y., A. Pai C. C., Chan A. S. C., J. Am. Chem. Soc., 1998, 120, 5808CrossRefGoogle Scholar
  12. [12]
    Uemura T., Zhang X., Matsumura K., Sayo N., Kumobayashi H., Ohta T., Nozaki K., Takaya H., J. Org. Chem., 1996, 61, 5510CrossRefGoogle Scholar
  13. [13]
    Fan Q. H., Liu G. H., Deng G. J., Chen X. M., Chan A. S. C., Tetra-hedron Lett., 2001, 42, 9047CrossRefGoogle Scholar
  14. [14]
    Yu H. B., Hu Q. S., Pu L., Tetrahedron Lett., 2000, 41, 1681CrossRefGoogle Scholar
  15. [15]
    Bartoszek M., Beller M., Deutsch J., Klawonn M., Köckritz A., Ne-mati N., Pews-Davtyan A., Tetrahedron, 2008, 64, 1316CrossRefGoogle Scholar
  16. [16]
    Liu D. C., Ouyang K. B., Yang N. F., Tetrahedron, 2016, 72, 1018CrossRefGoogle Scholar
  17. [17]
    Liu D. C., Zhu W. J., Zhang A. L., Yang N. F., Yang L. W., Chin. J. Org. Chem., 2015, 35, 1797CrossRefGoogle Scholar
  18. [18]
    Korostylev A., Tararov V. I., Fischer C., A., Börner A., J. Org. Chem., 2004, 69, 3220CrossRefGoogle Scholar
  19. [19]
    Jung H. I., Nandhakumar R., Yoon H. J., Lee S. G., Kim K. M., Jung H. I., Yoon H. J., Kim K. M., Bull. Korean Chem. Soc., 2010, 41, 1289CrossRefGoogle Scholar
  20. [20]
    Chen Y. H., Yang L. W., Yang N. F., Yang Z. S., Chem. Lett., 2014, 43, 1755CrossRefGoogle Scholar
  21. [21]
    Hatano M., Miyamoto T., Ishihara K., J. Org. Chem., 2006, 71, 6474CrossRefGoogle Scholar
  22. [22]
    Mori M., Nakai T., Tetrahedron Lett., 1997, 38, 6229CrossRefGoogle Scholar

Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany 2017

Authors and Affiliations

  1. 1.Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of ChemistryXiangtan UniversityXiangtanP. R. China

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