Stereospecific generation of α- and β-glycosyl-lithium reagents from glycosyl-stannanes: a stereocontrolled route to α- and β-C-glycosides

Abstract

Treatment of α- and β-D-tri-n-butylstannyl-glucopyranosides with n-butyl-lithium at –78 °C generates configurationally stable α-and β-D-glycosyl-lithium species which accept electrophilies with retention of configuration.