Beyond the Two-Conformer Model: The Role of Boat Conformers in the Stereoselectivity of SN1-Type Glycosylations

Key Points

• This research aims to explore how boat conformers affect the stereoselectivity of SN1-type glycosylations.
• Analyzed the behavior of glycosyl cations during glycosylation reactions.
• Compared the stereochemical outcomes of reactions involving different conformers.
• Investigated the impact of oxocarbenium ions on glycosylation selectivity.
• Glycosylations involving 4 H3-like cations showed α-selectivity.
• Boat conformers significantly influence the stereochemical outcomes of glycosylations.
• The study highlights the limitations of the traditional two-conformer model.