Abstract:

The anomeric effect, one of the classic stereoelectronic effects in organic chemistry, describes the preference of an electronegative substituent at the anomeric carbon of glycosides to adopt the axial configuration. Herein, we briefly survey the history and broad applications of the anomeric effect in organic synthesis. Particularly, we highlight the recent investigations on the related metallo-anomeric effect in carbohydrate chemistry and the possible strategies for its easy regulation via the alteration of the metal, oxidation state, ligand, and structure of the substrate. A positive interplay between scientific research and organic chemistry teaching would profoundly help students to understand the basic concepts and advanced applications of the metallo-anomeric effect.

Key words: Gauche effect, Anomeic effect, Stereoelectronic effect, Conformation