title: BH3-promoted stereoselective β-lithiation of N-alkyl-2-phenylaziridines.
abstract: BH(3) complexes of N-alkyl-2-phenylaziridines have been synthesized and their structure and stereochemistry proved with DFT calculations and NMR experiments. It has been demonstrated that the Lewis acid complexation is able to promote a regioselective β-lithiation in 2-phenylaziridino-borane complexes. The lithiated intermediates were configurationally stable, allowing an enantioselective preparation of cis-2,3-disubstituted aziridines.
authors.affiliation: Dipartimento di Chimica, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy.
authors.forename: Ugo
authors.initials: U
authors.lastname: Azzena
authors.forename: Giovanna
authors.initials: G
authors.lastname: Dettori
authors.forename: Luisa
authors.initials: L
authors.lastname: Pisano
authors.forename: Biagia
authors.initials: B
authors.lastname: Musio
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D001388:Aziridines; D001880:Boranes; D008094:Lithium