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Synthesis and Synthetic Applications of Samarium Enolates of Unmasked Amides: Efficient Synthesis of 3-Aminoamides and 3-Amino-2-chloroamides

José M. Concellón, Humberto Rodríguez-Solla*, Carmen Concellón, Carmen Simal, Noemí Alvaredo

*Dpto. Química Orgánica e Inorgánica, Universidad de Oviedo, C/ Julián Clavería 8, 33006 Oviedo, Spain, Email:

J. M. Concellón, H. Rodríguez-Solla, C. Concellón, C. Simal, N. Alvaredo, Synlett, 2010, 2119-2121.

DOI: 10.1055/s-0030-1258535

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Addition of in situ generated samarium acetamide and chloroacetamide enolates to aldimines afforded 3-aminoamides and 3-amino-2-chloroamides in high yields. A mechanism is proposed to explain the synthesis and reactivity of samarium enolates of primary amides.

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Aldol-type Reactions of Unmasked Iodoacetic Acid with Carbonyl Compounds Promoted by Samarium Diiodide: Efficient Synthesis of Carboxylic 3-Hydroxyacids and Their Derivatives

J. M. Concellón, C. Concellón, J. Org. Chem., 2006, 71, 4428-4432.

Key Words

amides, enolates, 3-aminoamides, samarium diiodide

ID: J60-Y2010-2460