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Chiral amido- and diamidophosphites with a peripheral pyridine ring in Pd-catalyzed asymmetric allylation

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Abstract

New chiral amidophosphite and diamidophosphite ligands with exocyclic pyridyl-containing substituents were obtained. Their efficiency in the Pd-catalyzed enantioselective allylic substitution was compared: in the sulfonylation of (E)-1,3-diphenylallyl acetate with sodium p-toluenesulfinate, the ee can reach 77%; its alkylation with dimethyl malonate and amination with pyrrolidine gave up to 80% and 74% ee, respectively. The asymmetric alkylation of cinnamyl acetate with ethyl 2-oxocyclohexanecarboxylate can provide to 68% ee. The complexation of zinc(ii) 5,10,15,20-tetraphenylporphyrinate with diamidophosphite ligand and its influence on conversion and enantioselectivity of the process were studied.

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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, I. M. Novikov & V. K. Gavrilov

  2. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Building. 4, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    I. A. Zamilatskov & I. S. Mikhel

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

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2278—2285, September, 2016.

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Gavrilov, K.N., Zheglov, S.V., Novikov, I.M. et al. Chiral amido- and diamidophosphites with a peripheral pyridine ring in Pd-catalyzed asymmetric allylation. Russ Chem Bull 65, 2278–2285 (2016). https://doi.org/10.1007/s11172-016-1578-6

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  • DOI: https://doi.org/10.1007/s11172-016-1578-6

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