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Theoretical study of the stereoselectivity in the reaction of 4-haloglutamic acid derivatives with arylamines

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Abstract

Diastereoselective nucleophilic substitution reaction of halogen in dimethyl (2S,4RS)-4-bromo- and 4-iodo-N-phthaloylglutamates with arylamines was studied within the framework of the electron density functional theory. According to calculations, the stereoselectivity of the substitution reaction with respect to (2S,4S)-isomers of 4-arylamino derivatives is determined not only by the steric hindrances in the transition state leading to minor (2S,4R)-diastereomers, but also by the stabilization of the corresponding initial reagents complex due to stacking interactions of the aromatic fragments of reagents.

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Funding

This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-43-660045), as well as within the framework of the state assignment of the Ministry of Science and Higher Education of the Russian Federation (Theme No. AAAA-A19-119011790134-1).

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620108, Ekaterinburg, Russian Federation

    M. A. Korolyova, A. Yu. Vigorov & V. P. Krasnov

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  1. M. A. Korolyova
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  2. A. Yu. Vigorov
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  3. V. P. Krasnov
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Corresponding author

Correspondence to M. A. Korolyova.

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No human or animal subjects were used in this research.

The authors declare no competing interests.

Based on the materials of the V International Conference “Modern synthetic methodologies for the design of drugs and functional materials” (November 8–12, 2021, Ekaterinburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1135–1142, June, 2022.

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Korolyova, M.A., Vigorov, A.Y. & Krasnov, V.P. Theoretical study of the stereoselectivity in the reaction of 4-haloglutamic acid derivatives with arylamines. Russ Chem Bull 71, 1135–1142 (2022). https://doi.org/10.1007/s11172-022-3513-3

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