title: Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation.
abstract: Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of β-products to α-products.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Nishikyo-ku Kyoto 615-8510 Japan.
authors.forename: Toshiki
authors.initials: T
authors.lastname: Nokami
authors.forename: Akito
authors.initials: A
authors.lastname: Shibuya
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Saigusa
authors.forename: Shino
authors.initials: S
authors.lastname: Manabe
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Ito
authors.forename: Jun-Ichi
authors.initials: J
authors.lastname: Yoshida