Ni(II)-Catalyzed Regio- and Stereoselective O-Alkylation for the Construction of 1,2-cis-Glycosidic Linkages

A transition-metal-catalyzed O-alkylation for the regio-and stereoselective construction of 1,2-cis-glycosidic linkages is presented. With nonprecious and readily available Ni(II) as a catalyst, 1,2-cis-glycosides were obtained via O-alkylation of 1,2-carbohydrate diols that can be accessed in a small number of steps. The tedious design of protecting groups or anomeric leaving groups could be avoided with this method. The strategy was applied for the efficient preparation of an important commercialized glycosidic compatible solute GG, its derivative MGG, and a branched alpha-glucan.

Automated summary

A transition-metal-catalyzed O-alkylation method was developed for the regio- and stereoselective construction of 1,2-cis-glycosidic linkages. Using nonprecious and readily available Ni(II) as a catalyst, 1,2-cis-glycosides were obtained via O-alkylation of 1,2-carbohydrate diols without the need for protecting groups or anomeric leaving groups.