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

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

*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, J. Org. Chem., 2007, 72, 7974-7979.

DOI: 10.1021/jo701417z (free Supporting Information)


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Abstract

A complete E-selective synthesis of α,β-unsaturated amides through a sequential reaction of a range of dichloroamides with a variety of aldehydes is promoted by Rieke manganese (Mn*). The unsaturated amides obtained are readily and efficiently transformed into α,β-unsaturated ketones, aldehydes, or carboxylic acids.


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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

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

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 Amides


ID: J42-Y2007-3260