Karaman H.S.Kılıç H.Şahin E.20.04.20192019-04-2020.04.20192019-04-2020170957-4166https://dx.doi.org/10.1016/j.tetasy.2017.09.004https://hdl.handle.net/20.500.12403/456The homogeneous asymmetric epoxidation of a range of enones was carried out using cumyl hydroperoxide, diethylzinc, and chiral pyrrolidinyl alcohol-containing ligands to afford the corresponding epoxy ketones with enantioselectivities of ?97% ee. Examination of the enantioselectivities obtained in the asymmetric epoxidation of enones using a range of chiral ligands indicated that synergy between the sterically bulky bicyclo[2.2.2]octane skeleton and the substituents attached to the carbinol moiety played an important role in determining the reaction enantioselectivity. The position and nature of the substituent on the aromatic ring of the enone also had a pronounced effect on the observed enantioselectivity. © 2017 Elsevier Ltdeninfo:eu-repo/semantics/closedAccesscumene hydroperoxidediethylzincenone derivativeketonemethanoloxygenpyrrolidine derivativepyrrolidinyl alcoholunclassified drugzinc complexArticleasymmetric synthesiscatalystchemical structurechiralitycontrolled studyenantiomerenantioselectivityepoxidationpriority journalreaction optimizationstoichiometrycumene hydroperoxidediethylzincenone derivativeketonemethanoloxygenpyrrolidine derivativepyrrolidinyl alcoholunclassified drugzinc complexArticleasymmetric synthesiscatalystchemical structurechiralitycontrolled studyenantiomerenantioselectivityepoxidationpriority journalreaction optimizationstoichiometryArticle28111626163210.1016/j.tetasy.2017.09.0042-s2.0-85030631055N/AWOS:000418981300017N/A