title: Enantioselective synthesis of gamma-aryl-gamma-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer-Villiger oxidation.
abstract: This paper describes an enantioselective synthesis of gamma-butyrolactones, using the N-tolyl-substituted oxazolidinone-containing ketone as catalyst and Oxone as oxidant via a sequential asymmetric epoxidation of benzylidenecyclopropanes, ring expansion, and Baeyer-Villiger oxidation. Up to 91% ee was obtained. Optically active cyclobutanones can also be obtained by suppressing the Baeyer-Villiger oxidation with use of more ketone catalyst and less Oxone.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Bin
authors.initials: B
authors.lastname: Wang
authors.forename: Yu-Mei
authors.initials: YM
authors.lastname: Shen
authors.forename: Yian
authors.initials: Y
authors.lastname: Shi
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D015107:4-Butyrolactone