The use of ultrastable Y zeolites in the Ferrier rearrangement of acetylated and benzylated glycals

Abstract

The Ferrier rearrangement of a selection of protected glycals was successfully performed using a commercially available H-USY zeolite CBV-720 as catalyst, selected after screening a range of similar catalysts. By incorporating either alcohols, thiophenol, trimethylsilyl azide or allyltrimethylsilane in the reaction it was shown that a range of O-, S-, N- and C-glycosides could be formed. With benzylated glucal and galactal in particular, use of the CBV-720 catalyst led to significantly higher yields of the 2,3-dehydroglycosides than previously reported.