Oxiranyl anion-mediated synthesis of highly enantiomerically enriched styrene oxide derivatives.
[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.
Capriati
Vito
V
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.
Florio
Saverio
S
Luisi
Renzo
R
Salomone
Antonio
A
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
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