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

A series of dimeric alpha,alpha,alpha',alpha'-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 H-1 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. (C) 2004 Elsevier Ltd. All rights reserved.