Chemical Research in Chinese Universities

, Volume 33, Issue 5, pp 746–752 | Cite as

FeCl3·6H2O-catalyzed synthesis of β-ketothioesters from chain α-oxo ketene dithioactals

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Abstract

A FeCl3·6H2O-catalyzed synthesis of β-ketothioesters from the hydrolysis reaction of chain α-oxoketene dithioacetals was carried out. Subsequently, we explored the FeCl3·6H2O-catalyzed Friedel-Crafts alkylation of the synthesized β-ketothioesters with alcohols in CH3CN at 25 °C, affording the desired α-alkylated β-ketothioesters in excellent yields. Wide scope of the substrates, use of inexpensive reagents, high yields under mild reaction conditions are notable features of these reactions.

Keywords

Iron(III) chloride Thioester Ketene dithioacetal Hydrolysis Friedel-Crafts alkylation 

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References

  1. [1]
    Ley S. V., Woodward P. R., Tetrahedron Lett., 1987, 28, 3019CrossRefGoogle Scholar
  2. [2]
    Fortner K. C., Shair M. D., J. Am. Chem. Soc., 2007, 129, 1032CrossRefGoogle Scholar
  3. [3]
    Bahlinger A., Fritz S. P., Wennemers H., Angew. Chem. Int. Ed., 2014, 53, 8779CrossRefGoogle Scholar
  4. [4]
    Das A., Khosla C., Acc. Chem. Res., 2009, 42, 631CrossRefGoogle Scholar
  5. [5]
    Chen A. Y., Schnarr N. A., Kim C. Y., Cane D. E., Khosla C., J. Am. Chem. Soc., 2006, 128, 3067CrossRefGoogle Scholar
  6. [6]
    Aron Z. D., Dorrestein P. C., Blackhall J. R., Kelleher N. L., Walsh C. T., J. Am. Chem. Soc., 2005, 127, 14986CrossRefGoogle Scholar
  7. [7]
    Duus F., Jakorsen P., Lawwwn S., Tetrahedron, 1968, 24, 5323CrossRefGoogle Scholar
  8. [8]
    Xin D., Burgess K. A., Org. Lett., 2014, 16, 2108CrossRefGoogle Scholar
  9. [9]
    Davis J. B., Bailey J. D., Sello J. K., Org. Lett., 2009, 11, 2984CrossRefGoogle Scholar
  10. [10]
    Hayashi Y., Miyamoto Y., Shoji M., Tetrahdron Lett., 2002, 43, 4079CrossRefGoogle Scholar
  11. [11]
    Yu H. F., Yu Z. K., Angew. Chem., Int. Ed., 2009, 48, 2929CrossRefGoogle Scholar
  12. [12]
    Yu H. F., Jin W. W., Sun C. L., Yu Z. K., Angew. Chem. Int. Ed., 2010, 49, 5792CrossRefGoogle Scholar
  13. [13]
    Liu Y., Barry B. D., Yu H. F., Liu J. Q., Liao P. Q., Bi X. H., Org. Lett., 2013, 15, 2608CrossRefGoogle Scholar
  14. [14]
    Fang Z. X., Liu Y., Barry B. D., Liao P. Q., Bi X. H., Org. Lett., 2015, 17, 782CrossRefGoogle Scholar
  15. [15]
    Yu H. F., Zhang Y. M., Li T. C., Liao P. Q., Diao Q. P., Xin G., Meng Q. L., Hou D. Y., RSC Adv., 2015, 5, 11293CrossRefGoogle Scholar
  16. [16]
    Ming W. B., Liu X. C., Wang L. J., Liu J., Wang M., Org. Lett., 2015, 17, 1746CrossRefGoogle Scholar
  17. [17]
    Luo H. M., Pan L., Xu X. X., Liu Q., J. Org. Chem., 2015, 80, 8282CrossRefGoogle Scholar
  18. [18]
    Jin W. W., Du W. M., Yang Q., Yu H. F., Yu Z. K., Org. Lett., 2011, 13, 4272CrossRefGoogle Scholar
  19. [19]
    Dong Y., Wang M., Liu J., Chem. Commun., 2011, 47, 7380CrossRefGoogle Scholar
  20. [20]
    Yu H. F., Liao P. Q., Tetrahedron Lett., 2016, 57, 2868CrossRefGoogle Scholar
  21. [21]
    Yu H. F., Wang D. L., Zhao H., Hou D. Y., Chin. J. Org. Chem., 2011, 31, 1949Google Scholar
  22. [22]
    Yu H. F., Chin. J. Chem., 2012, 23, 367CrossRefGoogle Scholar
  23. [23]
    Yu H. F., Liao P. Q., Chem. J. Chinese Universities, 2012, 33(9), 1969Google Scholar
  24. [24]
    Yu H. F., Synthetic Commun., 2013, 43, 1280CrossRefGoogle Scholar
  25. [25]
    Song Y., Tang X. S., Hou X. M., Bai Y., Chin. J. Org. Chem., 2013, 33, 76CrossRefGoogle Scholar
  26. [26]
    Yang Q., Wang L. D., Guo T. L., Yu Z. K., J. Org. Chem., 2012, 77, 8355CrossRefGoogle Scholar
  27. [27]
    Wang Y. M., Bi X. H., Li D. H., Liao P. Q., Wang Y. D., Yang J., Zhang Q., Liu Q., Chem. Commun., 2011, 47, 809CrossRefGoogle Scholar
  28. [28]
    Huang D. S., Wang H. N., Xue F. Z., Shi Y. A., J. Org. Chem., 2011, 76, 7269CrossRefGoogle Scholar
  29. [29]
    Yu H. F., Li T. C., Liao P. Q., Synthesis, 2012, 44, 3743CrossRefGoogle Scholar
  30. [30]
    Zhao H., Zhang F. W., Yu H. F., Liao P. Q., Diao Q. P., Li T. C., Xin G., Hou D. Y., Chin. J. Org. Chem., 2015, 35, 1493CrossRefGoogle Scholar
  31. [31]
    Yu H. F., Liao P. Q., Chem. Res. Chinese Universities, 2016, 32(3), 390CrossRefGoogle 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.School of Chemistry and Life ScienceAnshan Normal UniversityAnshanP. R. China
  2. 2.Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of ChemistryNortheast Normal UniversityChangchunP. R. China

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