Synthesis of a novel cage-functionalized chiral binaphthol host: a potential new agent for enantioselective recognition of chiral ammonium salts |
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Authors: | Alan P Marchand Hyun-Soon Chong Bishwajit Ganguly |
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Institution: | Department of Chemistry, University of North Texas, Denton, Texas 76203-5070, USA |
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Abstract: | Optically active, cage-functionalized crown ether (R)-3 which contains a 1,1′-bi-2-naphthol moiety has been prepared. Subsequently, the ability of (R)-3 to selectively recognize the enantiomers of guest ammonium salts, i.e., 4 and 5 in transport experiments was studied. Host (R)-3 displays significantly enhanced enantiomeric selectivity toward complex formation with 4 vis-à-vis complex formation with 5. The relative energetics of various relevant host–guest complexes have been investigated computationally. |
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