Water-promoted organic synthesis using glyco-organic substrates: the Claisen rearrangement

Abstract

The preparation of new glyco-organic substrates, along with their enhanced reactivity in water-promoted Claisen rearrangement, are described. The chirality induced by the glucose moiety during the course of the reaction is dependent upon the α- or β-configuration of the anomeric centre. This allowed us to prepare enantiomerically pure (R) or (S) 1,3-diols 8, with D-glucose, as the unique source of chirality.