Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)‐Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas
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| Natura: | Artículo Open Access |
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Wiley
2025
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| _version_ | 1867020236449906688 |
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| author | Sevgi Sarigul Ozbek Senel Teke Tuncel Sule Erol Gunal Ilknur Dogan |
| author_facet | Sevgi Sarigul Ozbek Senel Teke Tuncel Sule Erol Gunal Ilknur Dogan Sevgi Sarigul Ozbek Senel Teke Tuncel Sule Erol Gunal Ilknur Dogan |
| collection | Wiley Open Access |
| contents | Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)‐Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas Sevgi Sarigul Ozbek Senel Teke Tuncel Sule Erol Gunal Ilknur Dogan Chirality ABSTRACT2‐Thiohydantoin derivatives, including different substitutions at N‐1 and C‐5 (5‐methyl‐, 5‐isopropyl‐, 1‐acetyl‐5‐methyl‐, and 1‐acetyl‐5‐isopropyl‐) (1–4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2‐thiohydantions were obtained in the absence of any solvent via the reaction of L‐amino acids with thiourea (1&2) and via the reaction of L‐amino acids with NH4SCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2‐thiohydantoins were obtained although the same synthetic methods were used. The racemic nature of 2‐thiohydantoin derivatives (1–4) was proved by using 1H NMR analysis in the presence of (1R,2S)‐(−)‐ephedrine as a chiral auxiliary. In addition, the enantiomers of 3&4 were also resolved on chiral stationary phases by HPLC analyses. Furthermore, newly synthesized unsymmetrical chiral thioureas (S‐1&S‐2) and previously synthesized symmetrical ones (SS‐3&SS‐4) were used as chiral solvating agent (CSA) for the enantiodiscrimination of the thiohydantoins (5&6), previously reported. Optimal CSA/substrate ratios were determined for the best enantiodiscrimination. 10.1002/chir.70013 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| doi_str_mv | 10.1002/chir.70013 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_chir_70013 |
| institution | Wiley Open Access |
| license_str_mv | http://onlinelibrary.wiley.com/termsAndConditions#vor |
| publishDate | 2025 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)‐Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas Sevgi Sarigul Ozbek Senel Teke Tuncel Sule Erol Gunal Ilknur Dogan Chirality Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)‐Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas Sevgi Sarigul Ozbek Senel Teke Tuncel Sule Erol Gunal Ilknur Dogan Chirality ABSTRACT2‐Thiohydantoin derivatives, including different substitutions at N‐1 and C‐5 (5‐methyl‐, 5‐isopropyl‐, 1‐acetyl‐5‐methyl‐, and 1‐acetyl‐5‐isopropyl‐) (1–4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2‐thiohydantions were obtained in the absence of any solvent via the reaction of L‐amino acids with thiourea (1&2) and via the reaction of L‐amino acids with NH4SCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2‐thiohydantoins were obtained although the same synthetic methods were used. The racemic nature of 2‐thiohydantoin derivatives (1–4) was proved by using 1H NMR analysis in the presence of (1R,2S)‐(−)‐ephedrine as a chiral auxiliary. In addition, the enantiomers of 3&4 were also resolved on chiral stationary phases by HPLC analyses. Furthermore, newly synthesized unsymmetrical chiral thioureas (S‐1&S‐2) and previously synthesized symmetrical ones (SS‐3&SS‐4) were used as chiral solvating agent (CSA) for the enantiodiscrimination of the thiohydantoins (5&6), previously reported. Optimal CSA/substrate ratios were determined for the best enantiodiscrimination. 10.1002/chir.70013 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| title | Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)‐Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas |
| topic | Chirality |
| url | https://onlinelibrary.wiley.com/doi/10.1002/chir.70013 |