Tris(Pentafluorophenyl)Borane-Driven Stereoselective O-Glycosylation with Glycal Donors under Mild Condition

Abstract

Activation of glycal donors was achieved using tris(pentafluorophenyl)borane [B(C 6 F 5 ) 3 ] under mild reaction conditions. The glycosylation reaction proceeded efficiently with a wide range of sugar and non-sugar acceptors and provided α-selective glycosides in high yield. Interestingly, under different reaction conditions, Ferrier rearrangement products or 2-deoxyglycosides (i. e. addition products) were obtained as major products with benzyl-protected glycal donors. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim