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