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Bisdiamidophosphite with a bisoxazoline moiety in palladium-catalyzed enantioselective allylation

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Abstract

A bisdiamidophosphite ligand with stereogenic phosphorus atoms as a part of 1,3,2-diaza-phospholidine rings and a bisoxazoline backbone was synthesized and studied in the Pd-catalyzed asymmetric allylic substitution. The use of this ligand provided up to 93% ee in the alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate and up to 77% ee in the amination with pyrrolidine at quantitative conversion of the starting substrate.

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Authors and Affiliations

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

    K. N. Gavrilov, S. V. Zheglov, V. K. Gavrilov, I. D. Firsin & M. G. Maksimova

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. D. Firsin
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  5. M. G. Maksimova
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Correspondence to K. N. Gavrilov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1376–1379, July, 2019.

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Gavrilov, K.N., Zheglov, S.V., Gavrilov, V.K. et al. Bisdiamidophosphite with a bisoxazoline moiety in palladium-catalyzed enantioselective allylation. Russ Chem Bull 68, 1376–1379 (2019). https://doi.org/10.1007/s11172-019-2564-6

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  • DOI: https://doi.org/10.1007/s11172-019-2564-6

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