Stereoselective Synthesis of (Z)-β-Enamido Fluorides from N-Fluoroalkyl- and N-Sulfonyl-1,2,3-triazoles

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00543488" target="_blank" >RIV/61388963:_____/21:00543488 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/21:10430708
Result on the web
<a href="https://doi.org/10.1021/acs.orglett.1c01183" target="_blank" >https://doi.org/10.1021/acs.orglett.1c01183</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.orglett.1c01183" target="_blank" >10.1021/acs.orglett.1c01183</a>

Result language
angličtina
Original language name
Stereoselective Synthesis of (Z)-β-Enamido Fluorides from N-Fluoroalkyl- and N-Sulfonyl-1,2,3-triazoles
Original language description
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.
Czech name
—
Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/LTAUSA18037" target="_blank" >LTAUSA18037: Synthesis and reactivity of N-fluoroalkylated compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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