Sn-Free Ni-Catalyzed Reductive Coupling of Glycosyl Bromides with Activated Alkenes

Abstract

A mild, stereoselective method for the Ni-catalyzed synthesis of alpha-C-alkylglycosides is reported. This approach entails the reductive coupling of glycosyl bromides with activated alkenes at room temperature, with low alkene loading as an important feature. Diastereoselective coupling with 2-substituted acrylate derivatives was made possible through the use of 2,4-dimethyl-3-pentanol as a proton source.