A rapid, simple route to homochiral α,β-epoxyketones

Article abstract of DOI:10.1016/S0040-4039(99)01260-5

Substituted E- or Z-acrylylamides derived from a homochiral amine such as (R,R)-2,5-dimethylpyrrolidine or (S,S)-bis(2-phenylethyl)amine are readily epoxidised with complete stereocontrol with t-BuO₂Li to give two readily separated, enantiomerically pure diastereomeric epoxides. The easily separated epoxides are efficiently converted into α,β-epoxyketones by the action of organolithiums with 92->99% ee.