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: jmcg
uniovi.es
J. M. Concellón, H. Rodríguez-Solla, C. Simal, Org. Lett., 2008, 10, 4457-4460.
DOI: 10.1021/ol801607r
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Abstract
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
