The asymmetric Darzens reaction between aldehydes and (alpha)-haloesters is an effective method for the synthesis of glycidic esters. Chiral auxiliaries, chiral boron enolates, and asymmetric phase transfer catalysis have been used successfully to effect asymmetric induction in the Darzens reaction.
Diastereoselective epoxidations of chiral, non-racemic alkenes suffer from the limitation that removal of the auxiliary without disturbing the epoxide is often difficult. Nonetheless, diastereoselectivity is high in some cases.
Oxidation of epoxy alcohols generated via Sharpless epoxidation is a third method for the enantioselective synthesis of chiral α,β-epoxy carbonyl compounds. Swern and Parikh-Doering conditions are most commonly applied to accomplish these oxidations.