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Synthesis of New Chiral Secondary 1,2-Diamines Based on Levopimaric Acid and Their Use as Ligands in Copper(II)-Catalyzed Asymmetric Henry Reaction

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Abstract

Methods have been developed for the synthesis of new chiral imino amines and unsymmetrically substituted trans-1,2-diamines based on fumaropimaric acid. The new trans-1,2-diamines were tested as ligands in the copper(II)-catalyzed asymmetric Henry reaction of 4-nitrobenzaldehyde with nitromethane. The effect of substituents on the amino groups on the catalytic activity and asymmetric induction has been studied. The configuration of the major enantiomer has been found to be controlled by the size of substituents in the two amino groups of the ligand.

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Funding

This study was supported by the Ministry of Science and Higher Education of the Russian Federation (project no. AAAA-A17-117041710081-1).

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Authors and Affiliations

  1. Boreskov Institute of Catalysis Federal Research Center, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    V. N. Konev, Z. P. Pai & T. B. Khlebnikova

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  1. V. N. Konev
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  2. Z. P. Pai
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  3. T. B. Khlebnikova
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Correspondence to T. B. Khlebnikova.

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Konev, V.N., Pai, Z.P. & Khlebnikova, T.B. Synthesis of New Chiral Secondary 1,2-Diamines Based on Levopimaric Acid and Their Use as Ligands in Copper(II)-Catalyzed Asymmetric Henry Reaction. Russ J Org Chem 56, 604–612 (2020). https://doi.org/10.1134/S1070428020040077

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