Chemical Research in Chinese Universities

, Volume 34, Issue 3, pp 333–337 | Cite as

Chiral Phase-transfer Catalysts Bearing Multiple Hydrogen-bonding Donors Derived from Amino Acids: Efficient Catalysts for Diastereo- and Enantioselective Nitro-Mannich Reaction

  • Yu Liu
  • Zhonglin Wei
  • Yuxin Liu
  • Jingdong Wang
  • Jungang Cao
  • Dapeng Liang
  • Haifeng Duan
  • Yingjie Lin


Multiple hydrogen-bonding Phase-transfer catalyst Nitro-Mannich reaction Aldehyde-derived N-Boc ketimine 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

40242_2018_8005_MOESM1_ESM.pdf (9.2 mb)
Chiral phase-transfer catalysts bearing multiple hydrogen-bonding donors derived from amino acids : efficient catalysts for diastereo- and enantioselective nitro-Mannich reaction.


  1. [1]
    Takada K., Nagasawa K., Adv. Synth. Catal. 2009, 351(3), 345CrossRefGoogle Scholar
  2. [2]
    Sohtome Y., Takemura N., Takada K., Takagi R., Iguchi T., Naga-sawa K., Chem-Asian J., 2007, 2(9), 1150CrossRefPubMedGoogle Scholar
  3. [3]
    Sohtome Y., Hashimoto Y., Nagasawa K., Eur. J. Org. Chem., 2006, 2006(13), 2894CrossRefGoogle Scholar
  4. [4]
    Friestad G. K., Mathies A. K., Tetrahedron 2007, 63(12), 2541CrossRefGoogle Scholar
  5. [5]
    Ballini R., Petrini M., Tetrahedron 2004, 60(5), 1017CrossRefGoogle Scholar
  6. [6]
    Adam W., Makosza M., Saha-Möller C. R., Zhao C. G., Synlett. 1998, 1998(12), 1335CrossRefGoogle Scholar
  7. [7]
    Anderson J. C., Blake A. J., Howell G. P., Wilson C., J. Org. Chem., 2005, 70(2), 549CrossRefPubMedGoogle Scholar
  8. [8]
    Bennani Y. L., Hanessian S., Chem. Rev. 1997, 97(8), 3161CrossRefPubMedGoogle Scholar
  9. [9]
    Kizirian J. C., Chem. Rev. 2008, 108(1), 140CrossRefPubMedGoogle Scholar
  10. [10]
    Michalson E. T., Szmuszkovicz J., Progress in Drug Research, Springer, Berlin, 1989, 135CrossRefGoogle Scholar
  11. [11]
    Gravert D. J., Griffin J. H., J. Org. Chem., 1993, 58(4), 820CrossRefGoogle Scholar
  12. [12]
    Bernardi L., Bonini B. F., Dessole G., Fochi M., Comes-Franchini M., Gavioli S., Ricci A., Varchi G., J. Org. Chem., 2003, 68(4), 1418CrossRefPubMedGoogle Scholar
  13. [13]
    Tomioka K., Synthesis 1990, 1990(7), 541CrossRefGoogle Scholar
  14. [14]
    Albano V. G., Bandini M., Monari M., Marcucci E., Piccinelli F., Umani-Ronchi A., J. Org. Chem., 2006, 71(17), 6451CrossRefPubMedGoogle Scholar
  15. [15]
    Das A., Kureshy R. I., Maity N. C., Subramanian P. S., Khan N. H., Abdi S. H. R., Suresh E., Bajaj H. C., Dalton Trans. 2014, 43(32), 12357CrossRefPubMedGoogle Scholar
  16. [16]
    Uraguchi D., Oyaizu K., Noguchi H., Ooi T., Chem-Asian J., 2015, 10(2), 334CrossRefPubMedGoogle Scholar
  17. [17]
    Vara B. A., Mayasundari A., Tellis J. C., Danneman M. W., Arredondo V., Davis T. A., Min J., Finch K., Guy R. K., Johnston J. N., J. Org. Chem., 2014, 79(15), 6913CrossRefPubMedPubMedCentralGoogle Scholar
  18. [18]
    Xu X., Furukawa T., Okino T., Miyabe H., Takemoto Y., Chem-Asian J., 2006, 12(2), 466Google Scholar
  19. [19]
    Wang H. Y., Wang K. Y., Ren Y. F., Li N., Tang B., Zhao G., Adv. Synth. Catal. 2017, 359(11), 1819CrossRefGoogle Scholar
  20. [20]
    Liu Y. X., Liu Y., Wang J. D., Wei Z. L., Cao J. G., Liang D. P., Lin Y. J., Duan H. F., Tetrahedron Lett. 2017, 58(24), 2400CrossRefGoogle Scholar
  21. [21]
    Palomo C., Oiarbide M., Halder R., Laso A., López R., Angew. Chem. Int. Ed. 2006, 45(1), 117CrossRefGoogle Scholar
  22. [22]
    Tan C., Liu X. H., Wang L. W., Wang J., Feng X. M., Org. Lett. 2008, 10(22), 5305CrossRefPubMedGoogle Scholar
  23. [23]
    Nugent B. M., Yoder R. A., Johnston J. N., J. Am. Chem. Soc., 2004, 126(11), 3418CrossRefPubMedGoogle Scholar
  24. [24]
    Palomo C., Oiarbide M., Laso A., López R., J. Am. Chem. Soc., 2005, 127(50), 17622CrossRefPubMedGoogle Scholar
  25. [25]
    Uraguchi D., Sakaki S., Ooi T., J. Am. Chem. Soc., 2007, 129(41), 12392CrossRefPubMedGoogle Scholar
  26. [26]
    Handa S., Gnanadesikan V., Matsunaga S., Shibasaki M., J. Am. Chem. Soc., 2010, 132(13), 4925CrossRefPubMedGoogle Scholar
  27. [27]
    Gomez-Bengoa E., Linden A., López R., Múgica-Mendiola I., Oiarbide M., Palomo C., J. Am. Chem. Soc., 2008, 130(25), 7955CrossRefPubMedGoogle Scholar
  28. [28]
    Davis T. A., Wilt J. C., Johnston J. N., J. Am. Chem. Soc., 2010, 132(9), 2880CrossRefPubMedPubMedCentralGoogle Scholar
  29. [29]
    Rampalakos C., Wulff W. D., Adv. Synth. Catal., 2008, 350(11/12), 1785CrossRefPubMedPubMedCentralGoogle Scholar
  30. [30]
    Yamada K. i., Harwood S. J., Gröger H., Shibasaki M., Angew. Chem. Int. Ed. 1999, 38(23), 3504CrossRefGoogle Scholar
  31. [31]
    Wang B., Xu T., Zhu L., Lan Y., Wang J. D., Lu N., Wei Z. L., Lin Y. J., Duan H. F., Org. Chem. Front. 2017, 7(4), 1266CrossRefGoogle Scholar
  32. [32]
    Wei Y., He W., Liu Y. L., Liu P., Zhang S. Y., Org. Lett. 2012, 14(3), 704CrossRefPubMedGoogle Scholar
  33. [33]
    Johnson K. M., Rattley M. S., Sladojevich F., Barber D. M., Nuñez M. G., Goldys A. M., Dixon D. J., Org. Lett. 2012, 14(10), 2492CrossRefPubMedGoogle Scholar
  34. [34]
    Fini F., Sgarzani V., Pettersen D., Herrera R. P., Bernardi L., RicciA., Angew. Chem. 2005, 117(48), 8189CrossRefGoogle Scholar
  35. [35]
    Cao D. D., Chai Z., Zhang J. X., Ye Z. Q., Xiao H., Wang H. Y., Chen J. H., Wu X. Y., Zhao G., Chem. Commun. 2013, 49(53), 5972CrossRefGoogle Scholar
  36. [36]
    Jiang X. X., Zhang Y. F., Wu L., Zhang G., Liu X., Zhang H. L., Fu D., Wang R., Adv. Synth. Catal. 2009, 351(13), 2096CrossRefGoogle Scholar
  37. [37]
    Wang H. Y., Chai Z., Zhao G., Tetrahedron 2013, 69(25), 5104CrossRefGoogle Scholar
  38. [38]
    Wang H. Y., Zhang J. X., Cao, D. D., Zhao G., ACS Catalysis, 2013, 3(10), 2218CrossRefGoogle Scholar
  39. [39]
    Wang C. J., Dong X. Q., Zhang Z. H., J. Am. Chem. Soc., 2008, 130(27), 8606CrossRefPubMedGoogle Scholar
  40. [40]
    Davis T. A., Johnston J. N., Chem. Sci. 2011, 2(6), 1076CrossRefPubMedPubMedCentralGoogle Scholar
  41. [41]
    Lu N., Li R. X., Wei Z. L., Cao J. G., Liang D. P., Lin Y. J., Duan H. F., J. Org. Chem., 2017, 82(9), 4668CrossRefPubMedGoogle Scholar
  42. [42]
    Liu Y. L., Wang X., Wang X. Y., He W., Org. Biomol. Chem. 2014, 12(20), 3163CrossRefPubMedGoogle Scholar
  43. [43]
    Ma C. H., Kang T. R., He L., Liu Q. Z., Eur. J. Org. Chem., 2014, 2014(19), 3981CrossRefGoogle Scholar
  44. [44]
    Wu X. Y., Liu Q., Liu Y., Wang Q., Zhang Y., Chen J., Cao W. G., Zhao G., Adv. Synth. Catal. 2013, 355(13), 2701CrossRefGoogle Scholar
  45. [45]
    Dong Z., Yan C., Gao Y. Z., Dong C. E., Qiu G. F., Zhou H. B., Adv. Synth. Catal. 2015, 357(9), 2132CrossRefGoogle Scholar
  46. [46]
    Zhong F. R., Han X. Y., Wang Y. Q., Lu Y. X., Angew. Chem. 2011, 123(34), 7983CrossRefGoogle Scholar
  47. [47]
    Qiu S., Tan C. H., Jiang Z. Y., Beilstein J. Org. Chem., 2016, 12(1), 2293CrossRefPubMedPubMedCentralGoogle Scholar
  48. [48]
    Cowen B. J., Miller S. J., J. Am. Chem. Soc., 2007, 129(36), 10988CrossRefPubMedGoogle Scholar
  49. [49]
    Han X. Y., Wang Y. Q., Zhong F. R., Lu Y., J. Am. Chem. Soc., 2011, 133(6), 1726CrossRefPubMedGoogle Scholar
  50. [50]
    Han X. Y., Zhong F. R., Wang Y. Q., Lu Y. X., Angew. Chem. Int. Ed. 2012, 51(3), 767CrossRefGoogle Scholar
  51. [51]
    Huang, W. B., Tian H., Xu H., Zheng L. Y., Liu Q. W., Zhang S. Q., Catal. Lett. 2011, 141(6), 872CrossRefGoogle Scholar
  52. [52]
    Liu Y. X., Wei Z. L., Liu, Y., Cao J. G., Liang, D. P., Lin Y. J., Duan H. F., Org. Biomol. Chem. 2017, 15(43), 9234CrossRefPubMedGoogle Scholar
  53. [53]
    Wang B., Liu Y. X., Sun C., Wei Z. L., Cao J. G., Liang D. P., Lin Y. J., Duan H. F., Org. Lett. 2014, 16(24), 6432CrossRefPubMedGoogle Scholar
  54. [54]
    Dong X. Q., Teng H. L., Wang C. J., Org. Lett. 2009, 11(6), 1265CrossRefPubMedGoogle Scholar
  55. [55]
    Wang C. J., Zhang Z. H., Dong X. Q., Wu X. J., Chem. Commun. 2008, 130(12), 1431CrossRefGoogle Scholar
  56. [56]
    Shi X., He W., Li H., Zhang X., Zhang S. Y., Tetrahedron Lett. 2011, 52(25), 3204CrossRefGoogle Scholar

Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Yu Liu
    • 1
  • Zhonglin Wei
    • 1
  • Yuxin Liu
    • 1
  • Jingdong Wang
    • 1
  • Jungang Cao
    • 1
  • Dapeng Liang
    • 1
  • Haifeng Duan
    • 1
  • Yingjie Lin
    • 1
  1. 1.College of ChemistryJilin UniversityChangchunP. R. China

Personalised recommendations