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Metal-Free Halonium Mediated Acetate Shifts of Ynamides To Access α-Halo Acrylamides/Acrylimides

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posted on 2011-04-01, 00:00 authored 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.