Skip to main content
SpringerLink
Log in

Cu-OMS-2-catalyzed decarboxylation–acetoxylation of (3R,4R)-4-acid-3-[(R)-1-((t-butyl-dimethylsilyl)oxy)-ethyl]-1-methoxyphenyl-2-azetidinone with NaBrO3/NaOAc

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

(3R,4R)-4-Acetoxy-3-[(R)-1((t-butyldimethylsilyl)oxy)-ethyl]-1-methoxyphenyl-2-azetidinone (an important precursor for the synthesis of carbapenem antibiotics) was synthesized under mild and green conditions catalyzed by Cu-OMS-2. Normal to excellent isolated yields were obtained under given conditions.

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
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. H. Kwon, M.J. Lee, I.H. Lee et al., Bull. Korean Chem. Soc. 18, 475 (1997)

    CAS  Google Scholar 

  2. F. Cozzi, R. Annunziata, M. Cinquini et al., Chirality 10, 91 (1998)

    CAS  Google Scholar 

  3. G.I. Georg, J. Kant, H.S. Gill, J. Am. Chem. Soc. 109, 1129 (1987)

    Article  CAS  Google Scholar 

  4. G. Zhou, Y. Guan, H. Tang et al., Res. Chem. Intermed. 38, 251 (2012)

    Article  CAS  Google Scholar 

  5. M. Shiozaki, N. Ishida, Chem. Lett. 2, 169 (1983)

    Article  Google Scholar 

  6. S.-I. Murahashi, T. Naota, T. Kuwabara, JACS 112, 7820 (1990)

    Article  CAS  Google Scholar 

  7. G. Cainelli, P. Galletti, D. Giacomini, Tetrahedron Lett. 39, 7779 (1998)

    Article  CAS  Google Scholar 

  8. M. Laurent, M. Ceresiat, J. Marchand-Brynaert, J. Org. Chem. 69, 3194 (2004)

    Article  CAS  Google Scholar 

  9. J.M. Anderson, J.K. Kochi, J. Am. Chem. Soc. 92, 1651 (1970)

    Article  CAS  Google Scholar 

  10. L. Li, P. Yu, J. Cheng et al., Chem. Lett. 41, 600 (2012)

    Article  CAS  Google Scholar 

  11. X. Chen, X.-S. Hao, E. Charles et al., J. Am. Chem. Soc. 128, 6790 (2006)

    Article  CAS  Google Scholar 

  12. F. Schurz, J. Bauchert, T. Merker et al., Appl. Catal. A 355, 42 (2009)

    Article  CAS  Google Scholar 

  13. R. Wang, J. Li, Environ. Sci. Technol. 44, 4282 (2010)

    Article  CAS  Google Scholar 

  14. H. Huang, S. Sithambaram, C. Chen et al., Chem. Mater. 22, 3664 (2010)

    Article  CAS  Google Scholar 

  15. G.G. Xia, Y.G. Yin, W.S. Willis et al., J. Catal. 185, 91 (1999)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank Zhejiang Hisoar Pharmaceutical Co., Ltd for providing raw materials. This work was financially supported by the National Natural Science Foundation of China (20903047), and the Opening Project of State Key Laboratory of Chemical Resource Engineer (Beijing University of Chemical Technology).

Author information

Authors and Affiliations

  1. College of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou, 730050, China

    Guixian Li, Bingbing Peng & Zhihong Mao

  2. College of Biology and Chemical Engineering, Jiaxing University, Jiaxing, 314001, China

    Guang Qian

  3. State Key Laboratory of Chemical Resource Engineer, Beijing University of Chemical Technology, Beijing, 100029, China

    Shengfu Ji

Authors
  1. Guixian Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bingbing Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhihong Mao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Guang Qian
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shengfu Ji
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Guang Qian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, G., Peng, B., Mao, Z. et al. Cu-OMS-2-catalyzed decarboxylation–acetoxylation of (3R,4R)-4-acid-3-[(R)-1-((t-butyl-dimethylsilyl)oxy)-ethyl]-1-methoxyphenyl-2-azetidinone with NaBrO3/NaOAc. Res Chem Intermed 40, 293–298 (2014). https://doi.org/10.1007/s11164-012-0963-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0963-5

Keywords

Search

Navigation