Synthesis of novel C2-symmetric chiral crown ethers and investigation of their enantiomeric recognition properties |
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Authors: | Yilmaz Turgut Tarik Aral Halil Hosgoren |
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Affiliation: | University of Dicle, Faculty of Science, Department of Chemistry, 21280 Diyarbak?r, Turkey |
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Abstract: | A series of new C2-symmetric chiral aza crown ether macrocycles 1–4 have been synthesized from (S)-3-aryloxy-1,2-propanediol and (S)-1,2-propanediol for the enantiomeric recognition of amino acid ester derivatives. These new macrocycles have been shown to be strong complexing agents for primary organic ammonium salts (with K up to 176.93 M?1 and ΔG° up to 12.81 kJ mol?1) by 1H NMR titration. These macrocyclic host exhibited enantioselective bonding toward the d-enantiomer of phenylalanine methyl ester hydrochloride with KD/KL up to 6.87 in CDCl3 with 0.25% CD3OD. |
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