3-(2-Haloacyl)-2-oxazolidinones were shown to react with enals in an asymmetric SmI 2 -promoted Reformatsky reaction to give stereochemically well-defined 3-hydroxy-4-alkenyl-and 3-hydroxy-2-methyl-4-alkenyl imides. Chirality transfer of the Evans (S)-oxazolidinone unit via a Zimmerman−Traxler-like transition state resulted in Reformatsky products with a relative syn-configuration. The absolute configuration of compounds obtained is opposite to the corresponding products obtained via aldol addition of boron enolates to enals using the same Evans oxazolidinones.