Thioureas Derived from (S)-1-(2-pyridyl)ethylamine Enantiomer: Synthesis and Selected Applications as an Organocatalyst

Chrzanowski, Jacek; Sancineto, Luca; Deska, Malgorzata; Rachwalski, Michal; Drabowicz, Jozef

doi:10.3390/sym17020216

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Thioureas Derived from (S)-1-(2-pyridyl)ethylamine Enantiomer: Synthesis and Selected Applications as an Organocatalyst

by

Jacek Chrzanowski

¹

,

Luca Sancineto

²

,

Malgorzata Deska

³

,

Michal Rachwalski

⁴

and

Jozef Drabowicz

^1,3,*

¹

Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Division of Organic Chemistry, Sienkiewicza 112, 90-363 Lodz, Poland

²

Group of Catalysis, Synthesis and Organic Green Chemistry Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06123 Perugia, Italy

³

Institute of Chemistry, Jan Dlugosz University in Czestochowa, Armii Krajowej 13/15, 42-200 Czestochowa, Poland

⁴

Department of Organic and Applied Chemistry, University of Łodz, Tamka 12, 91-403 Łodz, Poland

^*

Author to whom correspondence should be addressed.

Symmetry 2025, 17(2), 216; https://doi.org/10.3390/sym17020216

Submission received: 15 December 2024 / Revised: 20 January 2025 / Accepted: 22 January 2025 / Published: 31 January 2025

(This article belongs to the Special Issue Asymmetric Centers in Optically Active Molecules Containing a Heteroatom)

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Abstract

In order to expand the group of chiral thiourea structures, several optically active thioureas derived from the (S)-1-(2-pyridyl)ethylamine enantiomer were prepared via its reaction with achiral or optically active isothiocyanates. To show their synthetic potential as chiral auxiliaries the isolated thioureas were tested as an optically active organocatalyst in the asymmetric version of the selected aldol condensation and addition of diethylzinc to benzaldehyde. The observation of asymmetric induction in these model reactions encourages further research on the use of this group of thioureas in asymmetric versions of multicomponent reactions and cycloadditions. The mechanistic aspects of the reactions under study are also briefly discussed.

Keywords: 1-(2-pyriydyl)ethylamine; optical resolution; asymmetric synthesis; chiral ligands; enantiomeric excess

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MDPI and ACS Style

Chrzanowski, J.; Sancineto, L.; Deska, M.; Rachwalski, M.; Drabowicz, J. Thioureas Derived from (S)-1-(2-pyridyl)ethylamine Enantiomer: Synthesis and Selected Applications as an Organocatalyst. Symmetry 2025, 17, 216. https://doi.org/10.3390/sym17020216

AMA Style

Chrzanowski J, Sancineto L, Deska M, Rachwalski M, Drabowicz J. Thioureas Derived from (S)-1-(2-pyridyl)ethylamine Enantiomer: Synthesis and Selected Applications as an Organocatalyst. Symmetry. 2025; 17(2):216. https://doi.org/10.3390/sym17020216

Chicago/Turabian Style

Chrzanowski, Jacek, Luca Sancineto, Malgorzata Deska, Michal Rachwalski, and Jozef Drabowicz. 2025. "Thioureas Derived from (S)-1-(2-pyridyl)ethylamine Enantiomer: Synthesis and Selected Applications as an Organocatalyst" Symmetry 17, no. 2: 216. https://doi.org/10.3390/sym17020216

APA Style

Chrzanowski, J., Sancineto, L., Deska, M., Rachwalski, M., & Drabowicz, J. (2025). Thioureas Derived from (S)-1-(2-pyridyl)ethylamine Enantiomer: Synthesis and Selected Applications as an Organocatalyst. Symmetry, 17(2), 216. https://doi.org/10.3390/sym17020216

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Thioureas Derived from (S)-1-(2-pyridyl)ethylamine Enantiomer: Synthesis and Selected Applications as an Organocatalyst

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