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Iron(II)/copper(I)-mediated stereoselective carbozincation of ynamides. One-pot synthesis of α-allyl-tetrasubstituted-enamides |
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| Authors: | Hugo Lingua François Vibert Dominique Mouysset Didier Siri Michèle P Bertrand Laurence Feray |
| Institution: | 1. Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, UMR 7273, Equipes CT, Avenue Normandie-Niemen, 13397 Marseille Cedex 20, France;2. Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, UMR 7273, Equipes CMO, Campus Saint-Jérôme, Avenue Normandie-Niemen, 13397 Marseille Cedex 20, France |
| 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. |
| Keywords: | Dialkylzinc Ynamides Carbometalation Copper (I) iodide Iron (II) chloride |
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