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Methyl (Z)-α-methoxyacrylates are generated in good yields by a mild, stereospecific two-carbon homologation of a wide variety of aldehydes utilizing commercial methyl 2,2-dichloro-2-methoxyacetate and CrCl 2 under Barbier conditions at room temperature. A rational mechanism based upon a Reformatsky-type addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.
Laboratoire de Synthèse Bio-Organique, UMR 7175-LC1, Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, 74 Route du Rhin, B.P. 24, 67401 Illkirch, France
Laboratoire de Synthèse Bio-Organique, UMR 7175-LC1, Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, 74 Route du Rhin, B.P. 24, 67401 Illkirch, France
Laboratoire de Synthèse Bio-Organique, UMR 7175-LC1, Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, 74 Route du Rhin, B.P. 24, 67401 Illkirch, France
Laboratoire de Synthèse Bio-Organique, UMR 7175-LC1, Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, 74 Route du Rhin, B.P. 24, 67401 Illkirch, France