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The First Sequential Reaction Promoted by Manganese: Complete Stereoselective Synthesis of (E)-α,β-Unsaturated Esters from 2,2-Dichloroesters and Aldehydes

José M. Concellón,* Humberto Rodríguez-Solla, Pamela Díaz and Ricardo Llavona

*Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellón, H. Rodríquez-Solla, P. Díaz, R. Llaona, J. Org. Chem., 2007, 72, 4396-4400.

DOI: 10.1021/jo070209w (free Supporting Information)


Abstract

A generally applicable, sequential reaction of dichloroesters with various aldehydes is promoted by active manganese to give α,β-unsaturated esters with complete control of stereoselectivity. The C-C double bond can be di- or trisubstituted. A mechanism based on a successive aldol-type reaction/-elimination is proposed.


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Sequential Reactions Promoted by Manganese: Completely Stereoselective Synthesis of (E)-α,β-Unsaturated Amides, Ketones, Aldehydes, and Carboxylic Acids

J. M. Concellón, H. Rodríquez-Solla, P. Díaz, J. Org. Chem., 2007, 72, 7974-7979.

An Easy, Efficient, and Completely Stereoselective Synthesis of (E)-α,β-Unsaturated Esters via Sequential Aldol-Type/Elimination Reactions Promoted by Samarium Diiodide or Chromium Dichloride

J. M. Concellón, C. Concellón, C. Méjica, J. Org. Chem., 2005, 70, 6111-6113.


Key Words

Manganese, α,β-Unsaturated Esters


ID: J42-Y2007-1830