title: Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride.
abstract: The ring opening of 2-substituted N,N-dibenzylaziridinium ions by bromide exclusively occurs at the substituted aziridine carbon atom in a stereospecific way, whereas the opposite regioselectivity was observed for hydride-induced ring opening at the unsubstituted position; furthermore, this unprecedented hydride-promoted reactivity was validated by means of Density Functional Theory (DFT) calculations.
authors.affiliation: Department of Chemistry, Sogang University, Seoul, Korea.
authors.forename: Sae Young
authors.initials: SY
authors.lastname: Yun
authors.forename: Saron
authors.initials: S
authors.lastname: Catak
authors.forename: Won Koo
authors.initials: WK
authors.lastname: Lee
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
authors.forename: Veronique
authors.initials: V
authors.lastname: Van Speybroeck
authors.forename: Michel
authors.initials: M
authors.lastname: Waroquier
authors.forename: Yongeun
authors.initials: Y
authors.lastname: Kim
authors.forename: Hyun-Joon
authors.initials: HJ
authors.lastname: Ha
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013379:Substrate Specificity; D013816:Thermodynamics
chemical_list: D001388:Aziridines; D001965:Bromides