Epoxidation of p-Methoxycinnamates Using Chiral Dioxiranes Derived from New Trisubstituted Halogenated Cyclohexanones: Enhanced Efficiency of Ketones Having an Axial Halogen
- 24 October 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (23) , 3531-3534
- https://doi.org/10.1021/ol0001721
Abstract
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 alpha-position (isopropyl instead of methyl) decreased the efficiency, and that the alpha-fluoro ketone 5a (axial fluorine) was the most efficient (82% conversion and 46% ee in (-)-epoxide).Keywords
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