Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives

摘要

The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an a anomer with high stereoselectivity. We have found that 3-0-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 —1.3:1.0 mixture of a and l anomers, indicating that a kinetic anomeric effect does not operate.