Addition reactions of iodomethyllithium to imines. A direct and efficient synthesis of aziridines and enantiopure amino aziridines.
An efficient and general synthesis of aziridines by the reaction of imines derived from p-toluenesulfonamides with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, is reported for the first time. The reaction with the chiral aldimine derived from phenylalaninal allowed access to (2R,1'S)-2-(1'-aminoalkyl)aziridine with very high diastereoselectivity, in enantiopure form. A mechanism to explain this novel reaction is proposed.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@uniovi.es
Rodríguez-Solla
Humberto
H
Simal
Carmen
C