n-Pentenyl esters facilitate an oxidative alternative to the Ferrier rearrangement. An expeditious route to sucrose

Abstract

Ferrier-type reactions can now be carried out under non-acidic conditions by treating 3-n-pentenoyl glycals with iodonium dicollidinium perchlorate whereupon the terminal double bond is chemoselectively activated to furnish an allylic oxo-carbenium ion which reacts at the anomeric position with monosaccharide alcohols to afford 2,3-unsaturated disaccharides in fairly good yields.