Stereoselective Synthesis of (Z)-β-Enamido Fluorides from N-Fluoroalkyl- and N-Sulfonyl-1,2,3-triazoles
| Autor: | Lukáš Janecký, Blanka Klepetářová, Petr Beier, Athanasios Markos, Radek Pohl |
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| Rok vydání: | 2021 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification 010405 organic chemistry Organic Chemistry Triazole Crystal structure 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Stereoselectivity Physical and Theoretical Chemistry Vinyl cation Fluoride Boron trifluoride |
| Zdroj: | Organic Letters. 23:4224-4227 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c01183 |
| Popis: | A reaction of N-sulfonyl-1,2,3-triazole with boron trifluoride etherate afforded a (Z)-β-ensulfonylamido fluoride instead of the previously erroneously assigned E isomer. The correction of the stereochemistry was based on a ge-1D ROESY NMR experiment and X-ray crystal structure analyses. Application of the reaction to N-fluoroalkyl-1,2,3-triazoles afforded new (Z)-β-enamido fluorides in a stereoselective manner. A mechanism involving coordination of BF3 with the triazole ring and vinyl diazonium and vinyl cation intermediates was proposed. |
| Databáze: | OpenAIRE |
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