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Enantioselective synthesis of 4,5-disubstituted pyrrolidin-2-one derivatives with two stereocenters on the basis of Michael adducts

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Chemistry of Heterocyclic Compounds Aims and scope

The addition of malonates to trans-β-alkyl-β-nitrostyrenes in the presence of chiral Mg2+ bisoxazoline complex and Ni2+ and Co2+ bis((S,S)- or (R,R)-N,N′-dibenzylcyclohexane-1,2-diamine) complexes resulted in the formation of Michael adducts with two stereo-centers which were used as key precursors for the preparation of potentially biologically active enantiopure 4,5-disubstituted pyrrolidin-2-one derivatives.

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This work was supported by the European Regional Development Fund Project No. 1.1.1.1./16/A/292.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV-1006, Latvia

    Natalja Orlova, Maxim Vorona, Vladislavs Baskevics, Marina Petrova, Sergey Belyakov, Helena Kazoka, Ruslan Muhamadejev & Grigory Veinberg

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  1. Natalja Orlova
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  2. Maxim Vorona
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  3. Vladislavs Baskevics
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  4. Marina Petrova
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  5. Sergey Belyakov
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  6. Helena Kazoka
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  7. Ruslan Muhamadejev
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  8. Grigory Veinberg
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Correspondence to Grigory Veinberg.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(8), 997–1009

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Orlova, N., Vorona, M., Baskevics, V. et al. Enantioselective synthesis of 4,5-disubstituted pyrrolidin-2-one derivatives with two stereocenters on the basis of Michael adducts. Chem Heterocycl Comp 56, 997–1009 (2020). https://doi.org/10.1007/s10593-020-02766-6

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