The role of cationic intermediates in the benzylidene-directed synthesis of 1,2-cis glycosidic linkages is unclear. Now cryogenic infrared spectroscopy provides insight into the SN1 mechanism of benzylidene-directed glycosylation reactions. The analysis reveals that cationic intermediates form anhydro cations through a two-step process, which correlates with the observed stereochemical outcome.
- Chun-Wei Chang
- Kim Greis
- Kevin Pagel