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Diastereomeric bisamidophosphites based on oxalamide 1,3-diol in asymmetric metal complex catalysis

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Abstract

Diastereomeric P*,P*-bisdiamidophosphite ligands of the 1,3,2-diazaphospholidine series bearing an oxalamide moiety have been synthesized. A possibility of their application in palladium- and rhodium-catalyzed asymmetric transformations was demonstrated. In Pd-catalyzed sulfonylation of (E)-1,3-diphenylallyl acetate with sodium p-toluenesulfinate enantioselectivity of up to 57% ee, in alkylation with dimethyl malonate of up to 77% ee, in amination with pyrrolidine of up to 78% ee, and in alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate of up to 52% ee, in Rh-catalyzed hydrogenation of (Z-methyl 2-acetamido-3-phenylacrylate of up to 88% ee was achieved. An effi ciency of diastereomeric chirality inducers was compared.

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Authors and Affiliations

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

    K. N. Gavrilov, I. V. Chuchelkin, S. V. Zheglov, V. K. Gavrilov, V. S. Zimarev, M. G. Maksimova & A. A. Shiryaev

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  1. K. N. Gavrilov
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  2. I. V. Chuchelkin
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  3. S. V. Zheglov
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  4. V. K. Gavrilov
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  5. V. S. Zimarev
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  6. M. G. Maksimova
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  7. A. A. Shiryaev
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Correspondence to K. N. Gavrilov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1376–1382, August, 2018.

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Gavrilov, K.N., Chuchelkin, I.V., Zheglov, S.V. et al. Diastereomeric bisamidophosphites based on oxalamide 1,3-diol in asymmetric metal complex catalysis. Russ Chem Bull 67, 1376–1382 (2018). https://doi.org/10.1007/s11172-018-2227-z

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  • DOI: https://doi.org/10.1007/s11172-018-2227-z

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