Synthesis and chiral recognition abilities of new calix[6]arenes bearing amino alcohol moieties

Herein the synthesis and recognition abilities towards amino acids and amino alcohols of new d-/l-phenylalaninol substituted p-tert-butylcalix[6]arenas are reported. These compounds, 6 and 7 have been synthesized via nucleophilic substitution reactions involving 5,11,17,23,29,35-tert-butyl-37,38-dimethoxy-39,40,41,42-(p-tosylethoxy)calix[6]arene 5 with d-/l-phenylalaninol in dry THF. The extraction properties of 6 and 7 towards some selected amino acid methylesters and amino alcohols have been studied by liquid–liquid extraction. These results show that chiral calix[6]arene derivatives exhibit a good affinity towards all amino acids and amino alcohols.

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5,11,17,23,29,35-tert-Butyl-37,38-dimethoxy-39,40,41,42-(d-1-hydroxy-3-phenyl-2-propylaminoethoxy)-calix[6]areneC112H148N4O10[α]D22=-3.9 (c 3.3, CHCl3)Source of chirality: d-phenylalaninol

5,11,17,23,29,35-tert-Butyl-37,38-dimethoxy-39,40,41,42-(l-1-hydroxy-3-phenyl-2-propylaminoethoxy)-calix[6]areneC112H148N4O10[α]D22=+4.2 (c 3.3, CHCl3)Source of chirality: l-phenylalaninol