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Aminoalkyl-phosphine (P,N) ligands with pentane-2,4-diyl backbone in asymmetric allylic substitution reactions

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Abstract

The asymmetric allylic substitution reaction of rac-1,3-diaryl-2-propenyl acetates with several C- and N-nucleophiles catalyzed by the palladium-complexes of eleven structurally analogous aminoalkyl-phosphines (P,N) with pentane-2,4-diyl backbone is reported. The role of the N-substituents and the influence of the ligand/palladium molar ratio on the activity and enantioselectivity of the catalytic system are studied. The solvent and the temperature dependence of the catalytic reaction were also assessed yielding enantioselectivities up to 95% in alkylation and 90% in amination processes under optimized reaction conditions.

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Acknowledgements

We thank Mr. Béla Édes for skilful assistance in analytical measurements and synthetic experiments and Dr. Imre Tóth for his useful comments on the manuscript. The research was supported by the ‘National Excellence Program’ in the framework of the Project TÁMOP-4.2.4.A/2-11/1-2012-0001 and by the National Research, Development and Innovation Office—NKFIH, K 115539.

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Pannonia, Egyetem u. 10, Veszprém, 8200, Hungary

    Zsófia Császár, Patrik Imre, Gergely Farkas & József Bakos

  2. NMR Laboratory, University of Pannonia, Egyetem u. 10, Veszprém, 8200, Hungary

    Szabolcs Balogh

  3. Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, Debrecen, 4032, Hungary

    Attila Bényei

Authors
  1. Zsófia Császár
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  2. Patrik Imre
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  3. Szabolcs Balogh
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  4. Attila Bényei
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  5. Gergely Farkas
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  6. József Bakos
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Corresponding author

Correspondence to József Bakos.

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Császár, Z., Imre, P., Balogh, S. et al. Aminoalkyl-phosphine (P,N) ligands with pentane-2,4-diyl backbone in asymmetric allylic substitution reactions. Monatsh Chem 148, 2069–2077 (2017). https://doi.org/10.1007/s00706-017-2029-2

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  • DOI: https://doi.org/10.1007/s00706-017-2029-2

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