A variety of -glycosides can be obtained from the fluoroarylborane (B(CF)) or silylium (RSi) catalyzed functionalization of 1-MeO- and per-TMS-sugars with TMS-X reagents. A one-step functionalization with a change as simple as the addition order and/or Lewis acid and TMS-X enables one to afford chiral synthons that are common (-pyranosides), have few viable synthetic methods (-furanosides), or are virtually unknown (anhydro--pyranosides), which mechanistically arise from whether a direct substitution, isomerization/substitution, or substitution/isomerization occurs, respectively.
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