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

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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.

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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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Correspondence to Frédéric Lamaty or Martin Kotora.

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Bednářová, E., Nečas, D., Císařová, I. et al. Synthesis of new bipyridine N,N′-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone. Monatsh Chem 150, 29–48 (2019). https://doi.org/10.1007/s00706-018-2289-5

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  • DOI: https://doi.org/10.1007/s00706-018-2289-5

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