title: Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids.
abstract: The asymmetric epoxidation of substituted cinnamic acids has been obtained in the presence of different keto bile acid derivatives as optically active carbonyl inducers and Oxone as oxygen source. Predominant or almost exclusive formation of both enantiomeric epoxides is obtained (ee up to 95%) depending on the specific substitution at carbons C(7) and C(12) of the bile acid.
authors.affiliation: Università di Ferrara, Dipartimento di Chimica, Via Borsari 46, 44100 Ferrara, Italy. brl@unife.it
authors.forename: Olga
authors.initials: O
authors.lastname: Bortolini
authors.forename: Giancarlo
authors.initials: G
authors.lastname: Fantin
authors.forename: Marco
authors.initials: M
authors.lastname: Fogagnolo
authors.forename: Roberto
authors.initials: R
authors.lastname: Forlani
authors.forename: Silvia
authors.initials: S
authors.lastname: Maietti
authors.forename: Paola
authors.initials: P
authors.lastname: Pedrini
mesh_terms: D001647:Bile Acids and Salts; D002934:Cinnamates / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007659:Ketones; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D001647:Bile Acids and Salts; D002934:Cinnamates; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007659:Ketones