Metal-Free Halonium Mediated Acetate Shifts of Ynamides To Access α-Halo Acrylamides/Acrylimides
datasetposted on 01.04.2011, 00:00 by Søren Kramer, Stig D. Friis, Zhuo Xin, Yann Odabachian, Troels Skrydstrup
A metal-free acetate shift of 3-acetoxy ynamides to access α-iodo, bromo, and chloro acrylamides/acrylimides under very mild conditions is demonstrated. The inherent alkyne activation of ynamides is sufficient to ensure the α-halo acrylamides/acrylimides in high yields without the addition of a catalyst. In all cases high Z-stereoselectivity is observed.