The design of inner-functionalised U-shaped cavity molecules: role of phenyl substituents at the 1,3-position of isobenzofurans and oxa-bridges in the dienophile as stereochemical controlling elements

Abstract

1,3-Diphenylisobenzofuran reacts with fused mono- and bis-norbornenes, 7-oxanorbornenes and cyclobutene-1,2-diesters with high stereospecifity whereas the corresponding isobenzofuran cycloadditions produce mixtures; this provides a basis for regulating geometry in the construction of polyalicyclic nanostructures.