The Bílik Reaction

The introduction of the Bilik reaction, the molybdic acid catalyzed interconversion of epimeric aldoses, is an important milestone in carbohydrate chemistry. The essentials of this unique, stereospecific carbon-skeleton rearrangement of epialdoses are presented. Emphasis is laid on the latest developments in the area, namely the mutual interconversion of 2-ketoses and 2-C-(hydroxymethyl)aldoses, a reaction that is exploited for the preparation of some important representatives of these reducing sugars. Mechanistic studies with isotopically substituted D-fructoses are also described.