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Epoxidation of p-Methoxycinnamates Using Chiral Dioxiranes Derived from New Trisubstituted Halogenated Cyclohexanones: Enhanced Efficiency of Ketones Having an Axial Halogen

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journal contribution
posted on 24.10.2000, 00:00 by A. Solladié-Cavallo, L. Bouérat
Epoxidation of p-methoxycinnamates using substoichiometric amounts of chiral and enantiopure dioxiranes generated in situ from chiral trisubstituted chloro and fluoro cyclohexanones showed that ketones with an axial Cl or F were more efficient than ketones with an equatorial Cl or F, that increasing the steric hindrance in the α-position (isopropyl instead of methyl) decreased the efficiency, and that the α-fluoro ketone 5a (axial fluorine) was the most efficient (82% conversion and 46% ee in (−)-epoxide).