One-step synthesis of rccc- and rctt-diastereomers of novel calix[4]resorcinols based on a para-thiophosphorylated derivative of benzaldehyde

Article abstract of DOI:10.1016/j.tetlet.2013.04.114

Novel calix[4]resorcinols with four 2-thioxo-1,3,2-dioxaphosphorinane fragments included in aromatic substituents have been synthesized via a one-step condensation of resorcinol and its derivatives with a new para- thiophosphorylated benzaldehyde. It has been found that the diastereomeric ratio depends substantially on the reaction conditions, in particular, the solvents and catalysts used. The macrocyclic products obtained are rctt- and/or rccc-isomers, which were isolated and the structures determined by NMR and single crystal X-ray diffraction studies.