An interpretation of the diastereofacial reactivity of (E)-3-trimethylsilyloxybuta-1,3-dien-1-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside based upon the exo-anomeric effect
Abstract
The geometry of the title diene has been probed by X-ray crystallography and by nuclear Overhauser effect difference spectroscopy; its diastereofacial discrimination in cycloadditions is ascribed to a reacting conformation determined by the exo-anomeric effect.