Skip to main content
SpringerLink
Log in

Mesoporous SBA-15 with Short Mesochannels Immobilized Natural Quinine for Asymmetric Michael Addition of Chalcones

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A heterogeneous catalyst of natural quinine supported on the mesoporous SBA-15 of short mesochannels was originally synthesized through a simple co-condensation approach for asymmetric organocatalysed Michael addition of malononitrile to chalcones. The catalytic activity was greatly enhanced, compared with the conventional analogue. Furthermore, the enantioselectivity could also be significantly improved for all substrates.

Graphical Abstract

Natural quinine was firstly immobilized on mesoporous SBA-15 with short mesochannels for the heterogeneous asymmetric Michael addition of malononitrile to chalcones. Compared with the conventional analogue, both the catalytic activity and enantioselectivity were greatly enhanced.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Dalko PI, Moisan L (2004) Angew Chem Int Ed 43:5138

    Article  CAS  Google Scholar 

  2. Ballini R, Bosica G, Fiorini D, Palmieri A, Petrini M (2005) Chem Rev 105:933

    Article  CAS  Google Scholar 

  3. Seayad J, List B (2005) Org Biomol Chem 3:719

    Article  CAS  Google Scholar 

  4. Taylor MS, Jacobsen EN (2006) Angew Chem Int Ed 45:1520

    Article  CAS  Google Scholar 

  5. Palomo C, Oiarbide M, Lopez R (2009) Chem Soc Rev 38:632

    Article  CAS  Google Scholar 

  6. Chen YC, Xue D, Deng JG, Cui X, Zhu J, Jiang YZ (2004) Tetrahedron Lett 45:1555

    Article  CAS  Google Scholar 

  7. Taylor MS, Zalatan DN, Lerchner AM, Jacobsen EN (2005) J Am Chem Soc 127:1313

    Article  CAS  Google Scholar 

  8. Li XF, Cun LF, Lian CX, Zhong L, Chen YC, Liao J, Zhu J, Deng JG (2008) Org Biomol Chem 6:349

    Article  CAS  Google Scholar 

  9. Yue L, Du W, Liu YK, Chen YC (2008) Tetrahedron Lett 49:3881

    Article  CAS  Google Scholar 

  10. Wang J, Li H, Zu LS, Jiang W, Xie HX, Duan WH, Wang W (2006) J Am Chem Soc 128:12652

    Article  CAS  Google Scholar 

  11. Shi J, Wang M, He L, Zheng K, Liu XH, Lin LL, Feng XM (2009) Chem Commun 4711

  12. Russo A, Perfetto A, Lattanzi A (2009) Adv Synth Catal 351:3067

    Article  CAS  Google Scholar 

  13. Bergbreiter DE (2002) Chem Rev 102:3345

    Article  CAS  Google Scholar 

  14. Dickerson TJ, Reed NN, Janda KD (2002) Chem Rev 102:3325

    Article  CAS  Google Scholar 

  15. Song CE, Lee SG (2002) Chem Rev 102:3495

    Article  CAS  Google Scholar 

  16. Trindade AF, Gois PMP, Afonso CAM (2009) Chem Rev 109:418

    Article  CAS  Google Scholar 

  17. Lee HM, Kim SW, Hyeon T, Kim BM (2001) Tetrahedron Asymmetr 12:1537

    Article  CAS  Google Scholar 

  18. Yu P, He J, Guo CX (2008) Chem Commun 2355

  19. Shen YB, Chen Q, Lou LL, Yu K, Ding F, Liu SX (2010) Catal Lett 137:104

    Article  CAS  Google Scholar 

  20. Sujandi, Park SE, Han DS, Han SC, Jin MJ, Ohsuna T (2006) Chem Commun 4131

  21. Cheng SF, Wang XG, Chen SY (2009) Top Catal 52:681

    Article  CAS  Google Scholar 

  22. Chen SY, Tang CY, Chuang WT, Lee JJ, Tsai YL, Chan JCC, Lin CY, Liu YC, Cheng SF (2008) Chem Mater 20:3906

    Article  CAS  Google Scholar 

  23. Chen SY, Chen YT, Lee JJ, Cheng SF (2011) J Mater Chem 21:5693

    Article  CAS  Google Scholar 

  24. Margolese D, Melero JA, Christiansen SC, Chmelka BF, Stucky GD (2000) Chem Mater 12:2448

    Article  CAS  Google Scholar 

  25. Aguado J, Arsuaga JM, Arencibia A (2008) Microporous Mesoporous Mater 109:513

    Article  CAS  Google Scholar 

  26. Yeoh FY, Matsumoto A, Baba T (2009) J Porous Mater 16:283

    Article  CAS  Google Scholar 

  27. Liu GH, Liu MM, Sun YQ, Wang JY, Sun CS, Li HX (2009) Tetrahedron Asymmetr 20:240

    Article  CAS  Google Scholar 

  28. Sheldon RA, Wallau M, Arends IWCE, Schuchardt U (1998) Acc Chem Res 31:485

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (20773069), the Specialized Research Fund for the Doctoral Program of Higher Education (200800551017 and 20100031120029), the Fundamental Research Funds for the Central Universities, and MOE (IRT-0927) for financial support.

Author information

Authors and Affiliations

  1. Institute of New Catalytic Materials Science and Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), College of Chemistry, Nankai University, Tianjin, 300071, People’s Republic of China

    Qiu Chen, Cui Xin, Lan-Lan Lou, Kai Yu, Fei Ding & Shuangxi Liu

Authors
  1. Qiu Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Cui Xin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lan-Lan Lou
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kai Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fei Ding
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Shuangxi Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shuangxi Liu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, Q., Xin, C., Lou, LL. et al. Mesoporous SBA-15 with Short Mesochannels Immobilized Natural Quinine for Asymmetric Michael Addition of Chalcones. Catal Lett 141, 1378–1383 (2011). https://doi.org/10.1007/s10562-011-0648-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-011-0648-5

Keywords

Search

Navigation