Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

Article abstract of DOI:10.1016/S0040-4039(97)00154-8

α-Hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic α-ketoesters 4 once or twice respectively by using NaBH₄ as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions.