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Synthesis of 1,2-diaminoadamantane and chiral ligands derived from it

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Abstract

A new synthesis of racemic 1,2-diaminoadamantane was accomplished, its resolution into enantiomers through diastereomeric salts with l-tartaric acid was carried out, which gave individual (S)-enantiomer in 26% yield. It was reacted with carbon disulfide to obtain (S)-octahydro-3a,7:5,9-dimethanocycloocta[d]imidazole-2(3H)-thione, for which an enantiomeric excess of 96% was determined by HPLC. The absolute (S)-configuration was inferred from the results of quantum mechanical calculations of optical rotation. A number of N-donor ligands were synthesized based on (S)-1,2-diaminoadamantane. The catalytic activity of their complexes with CuII, MnIII, and NiII was studied on the model Henry, Michael, and epoxidation reactions.

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Authors and Affiliations

  1. Samara State Technical University, 244 ul. Molodogvardeiskaya, 443100, Samara, Russian Federation

    P. A. Man’kova, V. A. Shiryaev, Ya. D. Shmel’kova, A. V. Moiseev, A. N. Reznikov & Yu. N. Klimochkin

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  1. P. A. Man’kova
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  2. V. A. Shiryaev
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  3. Ya. D. Shmel’kova
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  4. A. V. Moiseev
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  6. Yu. N. Klimochkin
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Correspondence to P. A. Man’kova.

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Additional information

This work was financially supported by the Russian Science Foundation (Project No. 21-73-20103). Calculations and studies by HPLC were carried out with the support of the Ministry of Science and Higher Education of the Russian Federation (Theme No. FSSE-2023-0003) within the framework of the Russian state assignment for the Samara State Technical University.

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1791–1801, August, 2023.

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Man’kova, P.A., Shiryaev, V.A., Shmel’kova, Y.D. et al. Synthesis of 1,2-diaminoadamantane and chiral ligands derived from it. Russ Chem Bull 72, 1791–1801 (2023). https://doi.org/10.1007/s11172-023-3961-4

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