Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives.Carbohydr Res. 2009 Mar 10; 344(4):516-20.CR
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.