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Total Regioselective Transformation of Aromatic Aziridine 2-Carboxamides into 2-Aminoamides Promoted by Active Manganese

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

*Departamento de Qumica Orgnica e Inorgnica, Facultad de Qumica, Universidad de Oviedo, Julin Clavera 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellón, H. Rodríguez-Solla, V. del Amo, P. Díaz, J. Org. Chem., 2010, 75, 2407-2410.

DOI: 10.1021/jo902708x (free Supporting Information)


Abstract

A totally regioselective transformation of aromatic N-4-methoxyphenylaziridine 2-carboxamides into 2-aminoamides is promoted by active manganese (Mn*). α-Amino ketones can be readily obtained by reaction of morpholine-derived 2-aminoamides with organolithium compounds.

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Key Words

α-amino amides, manganese, reduction


ID: J42-Y2010-0890