Iron(II)/copper(I)-mediated stereoselective carbozincation of ynamides. One-pot synthesis of alpha-allyl-tetrasubstituted-enamides - Aix-Marseille Université Access content directly
Journal Articles Tetrahedron Year : 2017

Iron(II)/copper(I)-mediated stereoselective carbozincation of ynamides. One-pot synthesis of alpha-allyl-tetrasubstituted-enamides

Abstract

The iron(II) chloride- and copper(I) iodide-mediated carbozincation of a panel of substituted ynamides is described in this article. The reaction is totally regio- and stereoselective. Experiments showed that the reaction mediated with Fe(II) was more substrate dependent than the reaction performed with Cu(I). Interestingly, in the presence of allylbromide, stereoselective carboallylation can be achieved for the first time in a one-pot procedure, leading to skipped dienamides.
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hal-01774256 , version 1 (14-05-2018)

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Hugo Lingua, Francois Vibert, Dominique Mouysset, Didier Siri, Michele P. Bertrand, et al.. Iron(II)/copper(I)-mediated stereoselective carbozincation of ynamides. One-pot synthesis of alpha-allyl-tetrasubstituted-enamides. Tetrahedron, 2017, 73 (25), pp.3415-3422. ⟨10.1016/j.tet.2017.04.065⟩. ⟨hal-01774256⟩
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