Metal-free halonium mediated acetate shifts of ynamides to access a-halo acrylamides/acrylimides

Abstract : A metal-free acetate shift of 3-acetoxy ynamides to access a-iodo, bromo, and chloro acrylamides/acrylimides under very mild conditions is demonstrated. The inherent alkyne activation of ynamides is sufficient to ensure the a-halo acrylamides/acrylimides in high yields without the addition of a catalyst. In all cases high Z-stereoselectivity is observed. © 2011 American Chemical Society.
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Submitted on : Wednesday, February 26, 2014 - 9:09:08 PM
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S. Kramer, S.D. Friis, Z. Xin, Yann Odabachian, T. Skrydstrup. Metal-free halonium mediated acetate shifts of ynamides to access a-halo acrylamides/acrylimides. Organic Letters, American Chemical Society, 2011, 13 (7), pp.1750-1753. ⟨10.1021/ol200269h⟩. ⟨hal-00951227⟩

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