Org. Biomol. Chem. [SOPhy]

Abstract

We developed a chemoselective metal-free access for the 1,2- and 2,3-semireduction of CF₃-N-allenamides. The enamide functionality of CF₃-substituted N-allenamides could be efficiently reduced by Et₃SiH/BF₃·OEt₂ in total regioselectivity and good stereoselectivity, whereas DBU promoted the isomerization of the resulting allyl amide leading exclusively to the E-configurated enamide.

Reference

Metal Free Regio – and Stereoselective Semireduction of CF3-Substituted N-Allenamides

Clément Gommenginger, Maxime Hourtoule, Marco Menghini and Laurence Miesch

Org. Biomol. Chem., 2024, Advance Article – DOI: https://doi.org/10.1039/D3OB01859H

 

Contact

Laurence Miesch (team SOPhy), Institut de Chimie de Strasbourg (UMR 7177).