title: One-pot preparation of piperazines by regioselective ring-opening of non-activated arylaziridines.
abstract: Herein we report a new straightforward synthesis of cis and trans 2,5-disubstituted N,N-dialkylpiperazines, even in enantioenriched form, by reacting non-activated N-alkyl arylaziridines in the presence of a catalytic amount of a Lewis acid. A stereochemical and NMR investigation revealed useful mechanistic insights for this process.
authors.affiliation: Dipartimento Farmaco-Chimico, Università degli Studi di Bari Aldo Moro, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy.
authors.forename: Piera
authors.initials: P
authors.lastname: Trinchera
authors.forename: Biagia
authors.initials: B
authors.lastname: Musio
authors.forename: Leonardo
authors.initials: L
authors.lastname: Degennaro
authors.forename: Anna
authors.initials: A
authors.lastname: Moliterni
authors.forename: Aurelia
authors.initials: A
authors.lastname: Falcicchio
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D058116:Lewis Acids; D010879:Piperazines