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Asymmetric α-chlorination of β-ketoesters using bifunctional ammonium salt catalysis

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Abstract

Chiral urea-quaternary ammonium salt hybrid organocatalysts were tested for their capability to control asymmetric α-chlorination reactions of β-ketoesters. After a careful screening we identified a structurally simple catalyst derivative that allowed us to obtain enantiomeric ratios up to 90:10 under operationally simple conditions using just 1 mol% of the catalyst.

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References

  1. Shibatomi K, Narayama A (2013) Asian J Org Chem 2:812

  2. Hintermann L, Togni A (2000) Helv Chim Acta 83:2425

    Article  CAS  Google Scholar 

  3. Li J, Pan W, Wang Z, Zhang X, Ding K (2012) Adv Synth Catal 354:1980

    Article  CAS  Google Scholar 

  4. Shibatomi K, Soga Y, Narayama A, Fujisawa I, Iwasa S (2012) J Am Chem Soc 134:9836

    Article  CAS  Google Scholar 

  5. Shibatomi K, Kotozaki M, Sasaki N, Fujisawa I, Iwasa S (2015) Chem Eur J 21:14095

    Article  CAS  Google Scholar 

  6. Cai Y, Wang W, Shen K, Wang J, Hu X, Lin L, Liu X, Feng X (2010) Chem Commun 46:1250

    Article  CAS  Google Scholar 

  7. Shirakawa S, Tokuda T, Kasai A, Maruoka K (2013) Org Lett 15:3350

    Article  CAS  Google Scholar 

  8. Luo J, Wu W, Xu L-W, Meng Y, Lu Y (2013) Tetrahedron Lett 54:2623

    Article  CAS  Google Scholar 

  9. Li Z, Yang F, Meng Q, Gao Z (2014) Tetrahedron Asymmetry 25:1215

    Article  CAS  Google Scholar 

  10. Liu RY, Wasa M, Jacobsen EN (2015) Tetrahedron Lett 56:3428

    Article  CAS  Google Scholar 

  11. Novacek J, Waser M (2014) Eur J Org Chem 802

  12. Tiffner M, Novacek J, Busillo A, Gratzer K, Massa A, Waser M (2015) RSC Adv 5:78941

    Article  CAS  Google Scholar 

  13. Shirakawa S, Maruoka K (2013) Angew Chem Int Ed 52:4312

  14. Novacek J, Waser M (2013) Eur J Org Chem 637

  15. Fernandez Gonzalez D, Brand JP, Mondiere R, Waser J (2013) Adv Synth Catal 355:1631

Download references

Acknowledgments

The used NMR spectrometers at JKU Linz were acquired in collaboration with the University of South Bohemia (CZ) with financial support from the European Union through the EFRE INTERREG IV ETC-AT-CZ program (project M00146, “RERI-uasb”). Financial support by the Federal State Government of Upper Austria (Research Fellowship to J. N.) is kindly acknowledged.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040, Linz, Austria

    Johanna Novacek & Mario Waser

  2. Institute of Inorganic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040, Linz, Austria

    Uwe Monkowius

  3. Institute of Analytical Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040, Linz, Austria

    Markus Himmelsbach

Authors
  1. Johanna Novacek
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  2. Uwe Monkowius
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  3. Markus Himmelsbach
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  4. Mario Waser
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Correspondence to Johanna Novacek or Mario Waser.

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Novacek, J., Monkowius, U., Himmelsbach, M. et al. Asymmetric α-chlorination of β-ketoesters using bifunctional ammonium salt catalysis. Monatsh Chem 147, 533–538 (2016). https://doi.org/10.1007/s00706-015-1604-7

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  • DOI: https://doi.org/10.1007/s00706-015-1604-7

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