ON THE USE OF 3-BROMOPROPYNE AS A REAGENT FOR THE INTRODUCTION OF THE PYRUVATE MOIETY

In the presence of metallic zinc 3-bromopropyne reacts with aldehydes to give homopropynylic alcohols which are converted to the corresponding bromohomopropynylic acetates by acetylation followed by reaction with N-bromosuccinimide and a catalytic quantity of silver acetate; these derivatives are then oxidized to gamma-acetoxy-alpha-ketoesters with osmium tetroxide and tert-butyl hydroperoxide resulting in a convenient four step sequence for the introduction of the pyruvate moiety.