title: Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives.
abstract: The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an alpha anomer with high stereoselectivity. We have found that 3-O-mesyl-D-glycals 2-4 were smoothly reacted with alcohols in the presence of triethylamine. The present reaction was shown to proceed under kinetic control to give approximately 1.3:1.0 mixture of alpha and beta anomers, indicating that a kinetic anomeric effect does not operate.
authors.affiliation: Graduate School of Integrated Science, Yokohama City University, Kanazawa-ku, Yokohama, Japan.
authors.forename: Yuhya
authors.initials: Y
authors.lastname: Watanabe
authors.forename: Tsubasa
authors.initials: T
authors.lastname: Itoh
authors.forename: Tohru
authors.initials: T
authors.lastname: Sakakibara
mesh_terms: D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006027:Glycosides