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Chemo- and Stereoselective Synthesis of Fluorinated Enamides from Ynamides in HF/pyridine: Second-Generation Approach to Potent Ureas Bioisosters

par Metayer, Benoit;Compain, Guillaume;Jouvin, Kevin;Martin-Mingot, Agnès;Bachmann, Christian;Marrot, Jérôme;Evano, Gwilherm ;Thibaudeau, Sébastien
Référence Journal of organic chemistry, 80, 7, page (3397-3410)
Publication Publié, 2015

Article révisé par les pairs

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Résumé :

(E)- and (Z)-α-fluoroenamides could be easily prepared with high levels of chemo- and regioselectivities by hydrofluorination of readily available ynamides with HF/pyridine. The scope and limitations of this new process for the hydrofluorination of ynamides, as well as the stability of the resulting α-fluoroenamides, have been extensively studied. Theoretical calculations at the MP2 and B3LYP levels of theory showed that the resulting fluoroenamides exhibit geometrical and electronic properties that partially mirror those of ureas, therefore demonstrating that the hydrofluorination of ynamides provides a general, straightforward, and user-friendly approach to bioisosteres of ureas, potent building blocks for biological studies and medicinal chemistry.