Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel alpha-fluoroenamides

alpha-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to alpha-fluoroenamides and can easily be applied to a wide range of substr...

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Published inChemical communications (Cambridge, England) Vol. 48; no. 42; pp. 5196 - 5198
Main Authors Compain, Guillaume, Jouvin, Kevin, Martin-Mingot, Agnes, Evano, Gwilherm, Marrot, Jerome, Thibaudeau, Sebastien
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.05.2012
Royal Society of Chemistry
Subjects
Amides - chemical synthesis
Amides - chemistry
Catalysis
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Fluorination
Halogenation
Hydrofluoric Acid - chemistry
Hydrofluorination
Organic chemistry
Other
Physical Sciences
Pyridines - chemistry
Quaternary Ammonium Compounds - chemistry
Science & Technology
Stereoisomerism
Synthesis
Ureas
UREA CLASS
HYDROGEN-FLUORIDE
CHEMISTRY
HF-SBF5
AGENTS
FLUORINATION
BOND
PROTEIN-KINASE INHIBITORS
CYCLIZATION
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Summary:alpha-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to alpha-fluoroenamides and can easily be applied to a wide range of substrates.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc31768k