Stereospecific beta-lithiation of oxazolinyloxiranes: synthesis of alpha,beta-epoxy-gamma-butyrolactones.
[reaction: see text]. Stereospecific beta-lithiation of beta-aryl-substituted oxazolinyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.
Capriati
Vito
V
Istituto di Chimica dei Composti OrganoMetallici-ICCOM, Dipartimento Farmaco-Chimico, Università di Bari, Via E.Orabona 4, I-70125 Bari, Italy.
Degennaro
Leonardo
L
Favia
Raffaele
R
Florio
Saverio
S
Luisi
Renzo
R
D015107:4-Butyrolactone / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D008094:Lithium; D015107:4-Butyrolactone