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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 1, pp 29–48 | Cite as

Synthesis of new bipyridine N,N′-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone

  • Eva Bednářová
  • David Nečas
  • Ivana Císařová
  • Michal Dušek
  • Frédéric LamatyEmail author
  • Martin KotoraEmail author
Original Paper

Abstract

Two methods for the synthesis of new axially chiral bipyridine N,N′-dioxides based on catalytic [2+2+2] cyclotrimerization of diynes with nitriles were developed. The N,N′-dioxides were used as catalysts in enantioselective allylation of benzaldehyde with allyltrichlorosilane and aldol reaction of trichlorosilyl ketene acetal of methyl acetate with acetophenone.

Graphical abstract

Keywords

Cyclotrimerization Catalysis N,N′-Dioxides Silicon compounds Enantioselective synthesis 

Notes

Acknowledgements

E. B. and M. K. would like to acknowledge financial support from the Czech Science Foundation (Grant no. 17-07707S) and French embassy in Prague. E. B. and F. L. would like to thank Université de Montpellier, CNRS and French Ministry of Higher Education and Research for funding.

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ScienceCharles UniversityPraha 2Czech Republic
  2. 2.Institut des Biomolécules Max Mousseron IBMM, UMR 5247, CNRS, Université de Montpellier, ENSCMMontpellier Cedex 5France
  3. 3.Department of Inorganic Chemistry, Faculty of ScienceCharles UniversityPraha 2Czech Republic
  4. 4.Institute of PhysicsCzech Academy of SciencesPraha 8Czech Republic

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