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Addition Reactions of Iodomethyllithium to Imines. A Direct and Efficient Synthesis of Aziridines and Enantiopure Amino Aziridines

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

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

J. M. Concellón, H. Rodríguez-Solla, C. Simal, Org. Lett., 2008, 10, 4457-4460.

DOI: 10.1021/ol801607r (free Supporting Information)

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The reaction of N-tosyl imines with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, allows an efficient and general synthesis of aziridines. A reaction of a chiral aldimine derived from phenylalaninal proceeded with high diastereoselectivity. A mechanism to explain this novel reaction is proposed.

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proposed mechanism

Key Words


ID: J54-Y2008-2850