The Diastereoselective Formation of Tetraalkoxy[4]resorcinarenes Derived from (-)-(2R)-2-Methoxy-2-phenylethanol and Proof of Absolute Configurations

The preparation of optically pure (-)-3-[(2R)-2-methoxy-2-phenylethoxy] phenol from resorcinol monobenzoate and its conversion into diastereoisomeric tetraalkoxyresorcin[4]arenes together with proof of the absolute configurations of the products is reported. The results of the study indicate that diastereoselective ring closure of linear tetrameric intermediates is controlled by the steric demand of the alkyl group in the precursor 3-alkoxyphenol