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Synthesis of 1-(Adamantan-1-yl)propane-1,2-diamine and Chiral Ligands Based Thereon

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Abstract

Racemic 1-(adamantan-1-yl)propane-1,2-diamine was synthesized from trans-2-(adamantan-1-yl)-3-methylaziridine, and its optical resolution was achieved with the use of L-malic acid. The isolated (1S,2R)-stereoisomer was derivatized with benzil, and enantiomeric purity of the resulting (2S,3R)-2-(adaman­tan-1-yl)-3-methyl-5,6-diphenyl-2,3-dihydropyrazine was determined by chiral HPLC. The reaction of (1S,2R)-1-(adamantan-1-yl)propane-1,2-diamine with carbon disulfide gave (4S,5R)-4-(adamantan-1-yl)-5-methylimidazolidine-2-thione whose absolute configuration was established by X-ray analysis. Racemic and optically pure (1S,2R)-1-(adamantan-1-yl)propane-1,2-diamines were used to obtain ligands and their metal complexes, and the latter were studied as catalysts in model epoxidation, Michael, and Henry reactions. Enantiodivergence was observed in the Henry reaction catalyzed by structurally related ligands.

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Scheme
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Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project nos. 20-33-90272, 20-53-04035). The spectral studies were financially supported by the Ministry of Science and Higher Education of the Russian Federation in the framework of the project part of state assignment no. 0778-2020-0005.

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Authors and Affiliations

  1. Samara State Technical University, 443100, Samara, Russia

    P. A. Mankova, A. N. Reznikov, V. A. Shiryaev, I. M. Tkachenko & Yu. N. Klimochkin

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  1. P. A. Mankova
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  2. A. N. Reznikov
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  3. V. A. Shiryaev
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Correspondence to P. A. Mankova.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 3, pp. 338–350 https://doi.org/10.31857/S0514749223030059.

Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee

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Mankova, P.A., Reznikov, A.N., Shiryaev, V.A. et al. Synthesis of 1-(Adamantan-1-yl)propane-1,2-diamine and Chiral Ligands Based Thereon. Russ J Org Chem 59, 383–394 (2023). https://doi.org/10.1134/S1070428023030053

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