Synthesis, NMR conformational studies and host–guest behaviour of new (+)-tartaric acid derivatives

Abstract

A series of dimeric α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol TADDOLs has been prepared and host–guest interactions of these structures have been characterized using a series of 1H NMR studies. Enantioselective recognition of the chiral alcohols glycidol and menthol was observed for phenyl and 2-naphthyl derivatives. The influence of steric bulk on the dynamic fluxional behaviour of the TADDOL structures was demonstrated by dynamic NMR.