The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of SN1 products, while nonpolar solvents favor SN2 products. Trichloroethylene was identified as the solvent most likely to give SN2 products in both C- and O-glycosylation reactions.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry