title: Addition reactions of chloro- or iodomethyllithium to imines. Synthesis of enantiopure aziridines and beta-chloroamines.
abstract: We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodo- or chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 degrees C. The reaction of in situ generated iodo- or chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino-1-chloroalkanes with high stereoselectivity.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071 Oviedo, Spain. jmcg@uniovi.es
authors.forename: José M
authors.initials: JM
authors.lastname: Concellón
authors.forename: Humberto
authors.initials: H
authors.lastname: Rodríguez-Solla
authors.forename: Pablo L
authors.initials: PL
authors.lastname: Bernad
authors.forename: Carmen
authors.initials: C
authors.lastname: Simal