Enantiomeric recognition and separation of chiral organic ammonium salts by chiral pyridino-18-crown-6 ligands

Jerald S. Bradshaw, Peter Huszthy, Tingmin Wang, Chengyue Zhu, Alexander Y. Nazarenko, Reed M. Izatt

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Optically pure allyloxy and dimethyl-substituted pyridino-18-crown-6 (8) was attached to silica gel by the following reactions. 4-Allyloxy-2,6-pyridinedimethyl ditosylate (23) was first prepared from chelidamic acid. Ditosylate 23 was treated with (S,S)-dimethyl(-substituted tetraethylene glycol to form 8. Ligand 8 was treated with triethoxysilane using a platinum catalyst. The resulting chiral crown-substituted triethoxysilane 32 was reacted with silica gel in toluene at 90° C to attach the crown to silica gel. Preliminary results of the separation of [a-(l-naphthyl)ethyl]ammonium perchlorate into its (R) and (S) forms using the bound chiral crown with acetone/methanol (7/3) (v/v) as the eluant are reported. The preparation of chiral dimethyl(allyloxyphenyl)pyridino-18-crown-6 (9) that could be attached to silica gel on the side opposite to the pyridine ring is also reported.

Original languageEnglish
Pages (from-to)267-275
Number of pages9
JournalSupramolecular Chemistry
Issue number3-4
Publication statusPublished - Jan 1 1993


ASJC Scopus subject areas

  • Chemistry(all)

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