title: Oxiranyl anion-mediated synthesis of highly enantiomerically enriched styrene oxide derivatives.
abstract: [reaction: see text] The stereospecific alpha-lithiation of optically active styrene oxides and the trapping reaction of the corresponding highly reactive intermediates with electrophiles to produce optically active styrene oxide derivatives are described. This methodology has been applied to the synthesis of an optically active oral antifungal agent of industrial interest.
authors.affiliation: C.N.R., Istituto di Chimica dei Composti OrganoMetallici-ICCOM, Sezione di Bari, Dipartimento Farmaco-Chimico, Università di Bari, Via E.Orabona 4, I-70126 Bari, Italy.
authors.forename: Vito
authors.initials: V
authors.lastname: Capriati
authors.forename: Saverio
authors.initials: S
authors.lastname: Florio
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
authors.forename: Antonio
authors.initials: A
authors.lastname: Salomone
mesh_terms: D017607:Aluminum Compounds; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005027:Ethylene Oxide / Q000737:chemistry*; D007202:Indicators and Reagents; D008024:Ligands; D018020:Lithium Compounds; D009682:Magnetic Resonance Spectroscopy; D019163:Reducing Agents; D013237:Stereoisomerism
chemical_list: D017607:Aluminum Compounds; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D008024:Ligands; D018020:Lithium Compounds; D019163:Reducing Agents; C042073:lithium aluminum hydride; C013690:styrene oxide; D005027:Ethylene Oxide