Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids.
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.
Bortolini
Olga
O
Università di Ferrara, Dipartimento di Chimica, Via Borsari 46, 44100 Ferrara, Italy. brl@unife.it
Fantin
Giancarlo
G
Fogagnolo
Marco
M
Forlani
Roberto
R
Maietti
Silvia
S
Pedrini
Paola
P
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
D001647:Bile Acids and Salts; D002934:Cinnamates; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007659:Ketones