Взаємодія N-(трет-бутилсульфініл)іміну трифторопірувату з діазометаном як зручний синтетичний підхід до енантіомерних трифторометиламінокислот
The interaction of enantiomerically pure N-tert-butylsulfinyl imines of trifluoropyruvate with diazomethane has been studied. It has been shown that there is the [3+2]-cycloaddition at the initial step with the formation of diastereomeric trifluoromethyltriazoline carboxylates in the ratio of 5.6:1....
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| Datum: | 2025 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | Englisch |
| Veröffentlicht: |
National University of Pharmacy
2025
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| Schlagworte: | |
| Online Zugang: | https://ophcj.nuph.edu.ua/article/view/343956 |
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| Назва журналу: | Journal of Organic and Pharmaceutical Chemistry |
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Journal of Organic and Pharmaceutical Chemistry| Zusammenfassung: | The interaction of enantiomerically pure N-tert-butylsulfinyl imines of trifluoropyruvate with diazomethane has been studied. It has been shown that there is the [3+2]-cycloaddition at the initial step with the formation of diastereomeric trifluoromethyltriazoline carboxylates in the ratio of 5.6:1. Treating the triazoline carboxylates with trifluoroacetic acid yielded optically pure aziridine carboxylates, which were subsequently converted into their corresponding acids. When subjected to hydrochloric acid in an ethereal solution, trifluoromethylaziridines underwent ring-opening and the sulfinyl group removal, producing α-chloromethylamino acids. The study also demonstrates the potential use of these aziridinecarboxylic acids in the peptide synthesis. |
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