Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives.
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.
Watanabe
Yuhya
Y
Graduate School of Integrated Science, Yokohama City University, Kanazawa-ku, Yokohama, Japan.
Itoh
Tsubasa
T
Sakakibara
Tohru
T
D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D006027:Glycosides