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

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

Research output: Contribution to journalArticle

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Abstract

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
Volume1
Issue number3-4
DOIs
Publication statusPublished - 1993

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Silica Gel
Ammonium Compounds
Salts
Ligands
Glycols
Toluene
Acetone
Platinum
Methanol
Catalysts
18-crown-6
triethoxysilane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantiomeric recognition and separation of chiral organic ammonium salts by chiral pyridino-18-crown-6 ligands. / Bradshaw, Jerald S.; Huszthy, P.; Wang, Tingmin; Zhu, Chengyue; Nazarenko, Alexander Y.; Izatt, Reed M.

In: Supramolecular Chemistry, Vol. 1, No. 3-4, 1993, p. 267-275.

Research output: Contribution to journalArticle

Bradshaw, Jerald S. ; Huszthy, P. ; Wang, Tingmin ; Zhu, Chengyue ; Nazarenko, Alexander Y. ; Izatt, Reed M. / Enantiomeric recognition and separation of chiral organic ammonium salts by chiral pyridino-18-crown-6 ligands. In: Supramolecular Chemistry. 1993 ; Vol. 1, No. 3-4. pp. 267-275.
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AU - Nazarenko, Alexander Y.

AU - Izatt, Reed M.

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