1.
Org Lett
; 16(14): 3684-7, 2014 Jul 18.
Artigo
em Inglês
| MEDLINE
| ID: mdl-24991982
RESUMO
The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.