Improved Enantioselectivity in the Epoxidation of Cinnamic Acid
Derivatives with Dioxiranes from Keto Bile Acids

Bortolini, Olga; Fantin, Giancarlo; Fogagnolo, Marco; Forlani, Roberto; Maietti, Silvia; Pedrini, Paola

doi:10.1021/jo020146b.s003

jo020146b_si_003.pdf (831.45 kB)

Improved Enantioselectivity in the Epoxidation of Cinnamic Acid Derivatives with Dioxiranes from Keto Bile Acids

journal contribution

posted on 2002-07-18, 00:00 authored by Olga Bortolini, Giancarlo Fantin, Marco Fogagnolo, Roberto Forlani, Silvia Maietti, Paola Pedrini

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.