Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
- Resource Type
- article
- Authors
- Toshiki Nokami; Akito Shibuya; Yoshihiro Saigusa; Shino Manabe; Yukishige Ito; Jun-ichi Yoshida
- Source
- Beilstein Journal of Organic Chemistry, Vol 8, Iss 1, Pp 456-460 (2012)
- Subject
- amino sugar
anomerization
electrochemical oxidation
glycosylation
thioglycoside
Science
Organic chemistry
QD241-441
- Language
- English
- ISSN
- 1860-5397
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.