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

Abstract

Indium-mediated allylation reactions of alpha-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-alpha -hydroxy acids. When the substituent of alpha-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 diastereo selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.