Preparation of homochiral phenolic crown ether having chiral subunits derived from (1R,2S)-cis-1,2,3,4-tetrahydronaphthalene-1,2-diol: temperature-dependent enantioselectivity in complexations with neutral amines

Crown ether (S,R,R,S)-1 containing chiral subunits derived from (1R,2S)-cis-1,2,3,4-tetrahydronaphthalene-1,2-diol and the phenol moiety bearing the intra-annular OH group and the 2,4-dinitrophenylazo group at its para-position have been prepared in enantiomerically pure form. The association constants for the complexes with chiral amines have been determined at various temperatures by the UV-visible spectroscopic method and thermodynamic parameters of complex formation have been calculated. (C) 1997 Elsevier Science Ltd.