title: Regio- and stereoselective lithiation and electrophilic substitution reactions of N-Alkyl-2,3-diphenylaziridines: solvent effect.
abstract: [structure: see text]. The lithiation reaction of cis- and trans-N-alkyl-2,3-diphenylaziridines has been investigated. While cis-diphenylaziridines do not undergo any lithiation upon treatment with organolithiums, the lithiation reaction of the trans counterparts is completely alpha-regioselective and the stereochemical course of the lithiation-trapping sequence is solvent dependent: inversion of configuration in coordinating solvents (THF or toluene/crown ether) and retention in hexane, ether, or toluene. The preparation of stereodefined functionalized N-alkyl-2,3-diphenylaziridines is described.
authors.affiliation: Dipartimento Farmaco-Chimico, Università di Bari, CNR, Istituto di Chimica dei Composti OrganoMetallici ICCOM, Sezione di Bari, Via E Orabona 4, I-70125 Bari, Italy.
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
authors.forename: Vito
authors.initials: V
authors.lastname: Capriati
authors.forename: Saverio
authors.initials: S
authors.lastname: Florio
authors.forename: Biagia
authors.initials: B
authors.lastname: Musio
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D004563:Electrochemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D009942:Organometallic Compounds; D012997:Solvents; D008094:Lithium