Chemocontrolled reduction of aromatic α-ketoesters by NaBH 4: Selective synthesis of α-hydroxy esters or 1, 2-diols

V Dalla, P Cotelle, JP Catteau

Index: Dalla, Vincent; Cotelle, Philippe; Catteau, Jean Pierre Tetrahedron Letters, 1997 , vol. 38, # 9 p. 1577 - 1580

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Citation Number: 25

Abstract

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.