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Diamidophosphite based on (1R,2R)-1,2-bis(3-hydroxybenzamido)cyclohexane in Pd-catalyzed enantioselective allylation

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Abstract

Diamidophosphite ligand bearing (1R,2R)-1,2-bis(3-hydroxybenzamido)cyclohexane fragment and stereogenic phosphorus atoms in the 1,3,2-diazaphopholidine cycles was synthesized. Catalytic performance of this ligand was evaluated in asymmetric allylic substitution. In the reactions involving (E)-1,3-diphenyl allyl acetate as a substrate, up to 94% ee in alkylation with dimethyl malonate and up to 68% ee in amination with pyrrolidine was achieved in the presence of this ligand.

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Authors and Affiliations

  1. S. A. Esenin Ryazan State University, 46 ul. Svobody, 390000, Ryazan, Russian Federation

    K. N. Gavrilov, S. V. Zheglov & V. K. Gavrilov

  2. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences, 31 Leninsky prosp., 119071, Moscow, Russian Federation

    I. A. Zamilatskov

Authors
  1. K. N. Gavrilov
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  2. S. V. Zheglov
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  3. V. K. Gavrilov
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  4. I. A. Zamilatskov
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Correspondence to K. N. Gavrilov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0680—0684, March, 2016.

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Gavrilov, K.N., Zheglov, S.V., Gavrilov, V.K. et al. Diamidophosphite based on (1R,2R)-1,2-bis(3-hydroxybenzamido)cyclohexane in Pd-catalyzed enantioselective allylation. Russ Chem Bull 65, 680–684 (2016). https://doi.org/10.1007/s11172-016-1355-6

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  • DOI: https://doi.org/10.1007/s11172-016-1355-6

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