Despite their prominence in biology, aminosugars present unique challenges in chemical synthesis due to their Lewis basic nature, which can often inhibit Lewis acidic catalysts and promoters required for glycosylation. Glycosylations using Nacetyl donors derived from 2-aminosugars are often especially problematic due to the formation of undesired 2-methyl-2-oxazoline byproducts derived from cyclization of the 2-aminoacyl group to the activated anomeric position under the glycosylation conditions. The oxazoline byproducts are typically quite stable even under forcing conditions with Lewis acids (Scheme 1). 11 Many of the approaches that employ N-acetyl glycosyl (GlycNAc) donors require stochiometric or super-stochiometric amounts of activators and long reaction times to overcome the innate challenges in this bond construction. Progress has been made to overcome this difficulty, through chemoenzymatic synthesis, 13 custom catalyst designs, 14 and variation of nitrogen protecting groups strategies. However, limitations remain including narrow substrate scope and preparative challenges that arise from moisture sensitivity, extended reaction times, and requirements for low-temperature control. With an eye towards developing a robust catalytic method for the assembly of aminoglycosides that proceeds with broad substrate scope and utilizes a simple, room-temperature catalytic procedure, we have examined the use of boron-catalyzed glycosylations using appropriately protected aminosugar donors and silyl ether acceptors as an alternative entry to this important class of glycosidic functionality. Scheme 1. Challenges and Current Approach to Aminoglycoside Synthesis.