Indium-mediated diastereoselective allylation reactions: preparation of tert-α-hydroxy acids

Abstract Indium-mediated allylation reactions of α-ketoimides derived from Oppolzer's sultam were accomplished in aqueous THF in good yields and excellent diastereomeric excesses. It could be a useful method for the preparation of enantiopure t -α-hydroxy acids. When the substituent of α-ketoimides was changed from phenyl to thiophenyl or furyl group, diastereoselectivity decreased in comparison to N -phenyl derivatives, but changing solvent to aqueous ethanol provided improved levels of diastereoselectivity.