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.
C. Gommenginger, M. Hourtoule, M. Menghini and L. Miesch, Org. Biomol. Chem., 2024, 22, 940 DOI: 10.1039/D3OB01859H
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