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Aldol reactions catalyzed by proline functionalized polyacrylonitrile fiber

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Abstract

A proline functionalized fiber catalyst was employed for aldol reactions in water. In the presence of the fiber catalyst, the aldol reactions proceeded smoothly at 40 °C and the products were obtained in excellent yields which were higher than those obtained for the reactions catalyzed by L-proline or trans-4-hydroxy-L-proline. This newly developed fiber catalyst is applicable to the reactions of a wide range of aromatic aldehydes and exhibits excellent reusability(up to 6 times) without any additional treatment.

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References

  1. Marhwald R., Modern Aldol Reactions, Wiley-VCH, Weinheim, 2004, 1

    Book  Google Scholar 

  2. Masamune S., Choy W., Petersen J. S., Sita L. R., Angew. Chem. Int. Ed. Engl., 1985, 24(1), 1

    Article  Google Scholar 

  3. Cai X., Wang Q., Yan C., Chem. Res. Chinese Universities, 2009, 25(5), 657

    CAS  Google Scholar 

  4. Liu B., Zhao D., Xu D., Xu Z., Chem. Res. Chinese Universities, 2007, 23(5), 549

    Article  Google Scholar 

  5. Trost B. M., Silcoff E. R., Ito H., Org. Lett., 2001, 3(16), 2497

    Article  CAS  Google Scholar 

  6. Yoshikawa N., Yamada Y. M. A., Das J., Sasai H., Shibasaki M., J. Am. Chem. Soc., 1999, 121(17), 4168

    Article  CAS  Google Scholar 

  7. Deng D., Wang L., Pei Y., Feng L., Liu C., Chem. Res. Chinese Universities, 2012, 28(1), 73

    CAS  Google Scholar 

  8. Nagase R., Matsumoto N., Hosomi K., Higashi T., Funakoshi S., Misaki T., Tanabe Y., Org. Biomol. Chem., 2007, 5(1), 151

    Article  CAS  Google Scholar 

  9. Nelson S. G., Tetrahedron: Asymmetry, 1998, 9(3), 357

    Article  CAS  Google Scholar 

  10. Zheng B. L., Liu Q. Z., Guo C. S., Wang X. L., He L., Org. Biomol. Chem., 2007, 5(18), 2913

    Article  CAS  Google Scholar 

  11. Zhou P. X., Luo S. Z., Cheng J. P., Org. Biomol. Chem., 2011, 9(6), 1784

    Article  CAS  Google Scholar 

  12. Dziedzic P., Zou W., Háfren J., Córdova A., Org. Biomol. Chem., 2006, 4(1), 38

    Article  CAS  Google Scholar 

  13. List B., Lerner R. A., Barbas III C. F., J. Am. Chem. Soc., 2000, 122(10), 2395

    Article  CAS  Google Scholar 

  14. Sakthivel K., Notz W., Bui T., Barbas III C. F., J. Am. Chem. Soc., 2001, 123(22), 5260

    Article  CAS  Google Scholar 

  15. List B., Tetrahedron, 2002, 58(28), 5573

    Article  CAS  Google Scholar 

  16. Pedrosa R., Andrés J. M., Manzano R., Román D., Téllez S., Org. Biomol. Chem., 2011, 9(3), 935

    Article  CAS  Google Scholar 

  17. Nakadai M., Saito S., Yamamoto H., Tetrahedron, 2002, 58(41), 8167

    Article  CAS  Google Scholar 

  18. Tang Z., Jiang F., Yu L. T, Cui X., Gong L. Z., Mi A. Q., Jiang Y. Z., Wu Y. D., J. Am. Chem. Soc., 2003, 125(18), 5262

    Article  CAS  Google Scholar 

  19. Gryko D., Saletra W. J., Org. Biomol. Chem., 2007, 5(13), 2148

    Article  CAS  Google Scholar 

  20. Gao J., Zheng L., Zhang S., Zhang X., Sun G., Qin L., Li Y., Liu Q., Li X., Chem. Res. Chinese Universities, 2010, 26(1), 50

    CAS  Google Scholar 

  21. Peng Y. Y., Ding Q. P., Li Z. C., Wang P. G., Cheng J. P., Tetrahedron Lett., 2003, 44(19), 3871

    Article  CAS  Google Scholar 

  22. Loh T. P., Feng L. C., Yang H. Y., Yang J. Y., Tetrahedron Lett., 2002, 43(48), 8741

    Article  CAS  Google Scholar 

  23. Gruttadauria M., Giacalone F., Marculescu A. M., Meo P. L., Riela S., Noto R., Eur. J. Org. Chem., 2007, (28), 4688

  24. Zou J., Zhao W. S., Li R. T., Zhang H. F., Cui Y. C., J. Appl. Polym. Sci., 2010, 118(2), 1020

    CAS  Google Scholar 

  25. Rodríguez-Llansola F., Miravet J. F., Escuder B., Chem. Commun., 2009, (47), 7303

  26. Yan J. C., Wang L., Chirality, 2009, 21(4), 413

    Article  CAS  Google Scholar 

  27. Massi A., Cavazzini A., Zoppo L. D., Pandoli O., Costa V., Pasti L., Giovannini P. P., Tetrahedron Lett., 2011, 52(5), 619

    Article  CAS  Google Scholar 

  28. Li G., Xiao J., Zhang W., Green Chem., 2011, 13(7), 1828

    Article  CAS  Google Scholar 

  29. Zhang L., Li Z., Chang R., Chen Y., Zhang W., React. Funct. Polym., 2009, 69(4), 234

    Article  CAS  Google Scholar 

  30. Badawy S. M., Dessouki A. M., J. Phys. Chem. B, 2003, 107(41), 11273

    Article  CAS  Google Scholar 

  31. Choudary B. M., Kantam M. L., Sreekanth P., Bandopadhyay T., Figueras F., Tuel A., J. Mol. Catal. A: Chem., 1999, 142(3), 361

    Article  CAS  Google Scholar 

  32. Wu F. C., Da C. S., Du Z. X., Guo Q. P., Li W. P., Yi L., Jia Y. N., Ma X., J. Org. Chem., 2009, 74(13), 4812

    Article  CAS  Google Scholar 

  33. Jiang J., Chen X. H., Wang J., Hui Y. H., Liu X. H., Lin L. L., Feng X. M., Org. Biomol. Chem., 2009, 7(21), 4355

    Article  CAS  Google Scholar 

  34. Jiang Z. Q., Yang H., Han X., Luo J., Wong M. W., Lu Y. X., Org. Biomol. Chem., 2010, 8(6), 1368

    Article  CAS  Google Scholar 

  35. Fernandez-Lopez R., Kofoed J., Machuqueiro M., Darbre T., Eur. J. Org. Chem., 2005, (24), 5268

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Correspondence to Wen-qin Zhang.

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Supported by the National Natural Science Foundation of China(No.20834002).

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Xiao, J., Li, Gw. & Zhang, Wq. Aldol reactions catalyzed by proline functionalized polyacrylonitrile fiber. Chem. Res. Chin. Univ. 29, 256–262 (2013). https://doi.org/10.1007/s40242-013-2236-2

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  • DOI: https://doi.org/10.1007/s40242-013-2236-2

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