A publicação do mês.

O trabalho de superácido grupo da equipe Síntese Orgânica fazer a cobertura da JOC (The Journal of Organic Chemistry).
Este trabalho, em colaboração com C. Bachmann (IC2MP) e G. Evano (ULB-Bruxelas), como parte da tese de Benoit Metayer (ANR VINFLUSUP jovens investigadores) lida com a síntese de compostos vinílicos fluorados por hidrofluoração em ynamides presença de HF / piridina. Estes compostos são fluorovyniliques novas funções mime uréia fluorados, motivos presentes em muitos compostos bioativos.

joceah_v080i007.indd

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

Superacid Group in Organic Synthesis Team, Université de Poitiers, CNRS UMR 7285 IC2MP wrote a new article in The Journal of Organic Chemistry.

Authors are Benoît Métayer, Guillaume Compain, Kévin Jouvin, Agnès Martin-Mingot, Christian Bachmann, Jérôme Marrot, Gwilherm Evano, and Sébastien Thibaudeau.

 

Abstract

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.

 

Lire l’article : http://pubs.acs.org/doi/abs/10.1021/jo502699y

 

JOC cover april

 

 

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