Skip to main content
SpringerLink
Log in

Promiscuous Lipase-Catalyzed C–C Bond Formation Reactions Between 4 Nitrobenzaldehyde and 2-Cyclohexen-1-one in Biphasic Medium: Aldol and Morita–Baylis–Hillman Adduct Formations

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Lipases catalyzed the reaction between 4-nitrobenzaldehyde and 2-cyclohexen-1-one in aqueous-DMSO co-solvent mixtures to give Morita–Baylis–Hillman product and aldol product. Among lipases, Burkholderia cepacia lipase gave the best overall conversion of 96 % in 50 % (v/v) DMSO while Mucor javanicus lipase showed highest stereoselectivity in the formation of the aldol (79 % ee) and Morita–Baylis–Hillman product (63 % ee) with 30 % (v/v) DMSO.

Graphical Abstract

Lipase catalysed Morita–Baylis–Hillman reaction

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
Scheme 2

Similar content being viewed by others

References

  1. Singh A, Chisti Y, Banerjee UC (2012) Process Biochem 47:2398–2404

    Article  CAS  Google Scholar 

  2. Othman SS, Basri M, Hussein MZ, Rahman MBA, Jasmani H, Rahman RNZRA, Salleh AB (2008) Food Chem 106:437–443

    Article  CAS  Google Scholar 

  3. Rahman MBA, Zaidan US, Basri M, Salleh AB, Rahman RNZRA, Hussein MZ (2008) J Mol Catal B: Enzym 50:33–39

    Article  Google Scholar 

  4. Adlercreutz P (2013) Chem Soc Rev 42:6406–6436

    Article  CAS  Google Scholar 

  5. Gotor V, Alfonso I, Uradiales EG (2008) Asymmetric organic synthesis with enzymes. Wiley-VCH Verlag, Weinheim

    Book  Google Scholar 

  6. Hult K, Berglund P (1987) Trends Biotechnol 25:231–238

    Article  Google Scholar 

  7. Yang F, Wang Z, Wang H, Zhang H, Yue H, Wang L (2014) R Soc Chem Adv 4:25633–25636

    CAS  Google Scholar 

  8. Gupta MN, Kapoor M, Majumder AB, Singh V (2011) Curr Sci 100:1152–1163

    CAS  Google Scholar 

  9. Kapoor M, Gupta MN (2012) Process Biochem 47:555–569

    Article  CAS  Google Scholar 

  10. Majumder A, Gupta MN (2014) Synth Commun 44:818–826

    Article  CAS  Google Scholar 

  11. Wang H, Wang Z, Wang C, Yang F, Zhang H, Yue H, Wang L (2014) R Soc Chem Adv 4:35686–35689

    CAS  Google Scholar 

  12. Langer P (2000) Angew Chem Int Ed 39:3049–3052

    Article  CAS  Google Scholar 

  13. Shi Y-L, Shi M (2007) Eur J Org Chem 18:2905–2916

    Article  Google Scholar 

  14. Basavaiah D, Veeraraghavaiah G (2012) Chem Soc Rev 41:68–78

    Article  CAS  Google Scholar 

  15. Reetz MT, Mondiere R, Carballeira JD (2007) Tetrahedron Lett 48:1679–1681

    Article  CAS  Google Scholar 

  16. Lopez-Iglesias M, Busto E, Gotor V, Gotor-Fernandes V (2011) Adv Synth Catal 353:2345–2353

    Article  CAS  Google Scholar 

  17. Jiang L, Yu H-W (2014) Biotechnol Lett 36:99–103

    Article  CAS  Google Scholar 

  18. Li K, He T, Li C, Feng X-W, Wang N, Yu X-Q (2009) Green Chem 11:777–779

    Article  CAS  Google Scholar 

  19. de Souza ROMA, Matos LMC, Gonçalves KM, Costa ICR, Babics I, Leite SGF, Oestreicher EG, Antunes OAC (2009) Tetrahedron Lett 50:2017–2018

    Article  Google Scholar 

  20. Arora B, Pandey PS, Gupta MN (2014) Tetrahedron Lett 55:3920–3922

    Article  CAS  Google Scholar 

  21. Majumder AB, Ramesh NG, Gupta MN (2009) Tetrahedron Lett 50:5190–5193

    Article  CAS  Google Scholar 

  22. Kataoka T, Iwama T, Tsujiyama S-I, Iwamura T, Watanabe S-I (1998) Tetrahedron 54:11813–11824

    Article  CAS  Google Scholar 

  23. Luo S, Zhang B, He J, Janezuk A, Wang PG, Cheng J-P (2002) Tetrahedron Lett 43:7361–7369

    Article  Google Scholar 

  24. Wu W-B, Xu J-M, Wu Q, Lv D-S, Lin X-F (2006) Adv Synth Catal 348:487–492

    Article  CAS  Google Scholar 

  25. Wang J-L, Liu B-K, Yin C, Wu Q, Lin X-F (2011) Tetrahedron 67:2689–2692

    Article  CAS  Google Scholar 

  26. Lanne C (1987) Biocatalysis 30:17–22

    Article  Google Scholar 

  27. Gupta MN (1992) Eur J Biochem 203:25–32

    Article  CAS  Google Scholar 

  28. Carrea G, Riva S (2000) Angew Chem Int Ed 39:2226–2254

    Article  CAS  Google Scholar 

  29. Khmelnitsky YL, Mozhaev VV, Belova AB, Sergeeva MV, Martinek K (1991) Eur J Biochem 198:31–41

    Article  CAS  Google Scholar 

  30. McDougal NT, Trevellini WL, Rodgen SA, Kliman LT, Schaus SE (2004) Adv Synth Catal 346:1231–1240

    Article  CAS  Google Scholar 

  31. Svedendahl M, Carlqvist P, Branneby C, Allner O, Frise A, Hult K, Berglund P, Brinck T (2008) ChemBioChem 9:2443–2451

    Article  CAS  Google Scholar 

  32. Torre O, Alfonso I, Gotor V (2004) Chem Commun 1724–1725

  33. Carlqvist P, Svedendahl M, Branneby C, Hult K, Brinck T, Berglund P (2005) ChemBioChem 6:331–336

    Article  CAS  Google Scholar 

  34. Khersonsky O, Tawfik DS (2010) Ann Rev Biochem 79:471–505

    Article  CAS  Google Scholar 

  35. Gatri R, El Gaied MM (2002) Tetrahedron Lett 43:7835–7836

    Article  CAS  Google Scholar 

  36. Rastogi N, Namboothiri INN, Cojocaru M (2004) Tetrahedron Lett 45(24):4745–4748

    Article  CAS  Google Scholar 

  37. Bjelic S, Nivon LG, Çelebi-Olçum N, Kiss G, Rosewall CF, Lovick HM, Ingalls EL, Gallaher JL, Seetharaman J, Lew S, Montelione GT, Hunt JF, Michael FE, Houk KN, Baker D (2013) ACS Chem Biol 8:749–757

    Article  CAS  Google Scholar 

  38. Branneby C, Carlqvist P, Magnusson A, Hult K, Brinck T, Berglund P (2003) J Am Chem Soc 125:874–875

    Article  CAS  Google Scholar 

  39. Shi M, Liu X-G (2008) Org Lett 10:1043–1046

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The work was supported by financial support of the Department of Science and Technology (DST), Govt. of India (Grant No.: SR/SO/BB-68/2010).

Author information

Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110 016, India

    Manali Kapoor

  2. Department of Chemistry, Rajiv Gandhi University of Knowledge Technologies, Basar Campus, Basar, 504107, Telangana, India

    Abir B. Majumder

  3. Department of Biochemical Engineering & Biotechnology, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110 016, India

    Munishwar Nath Gupta

Authors
  1. Manali Kapoor
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Abir B. Majumder
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Munishwar Nath Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Munishwar Nath Gupta.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 125 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kapoor, M., Majumder, A.B. & Gupta, M.N. Promiscuous Lipase-Catalyzed C–C Bond Formation Reactions Between 4 Nitrobenzaldehyde and 2-Cyclohexen-1-one in Biphasic Medium: Aldol and Morita–Baylis–Hillman Adduct Formations. Catal Lett 145, 527–532 (2015). https://doi.org/10.1007/s10562-014-1429-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-014-1429-8

Keywords

Search

Navigation