Enantiomerically pure chiral phenazino-crown ethers: synthesis,preliminary circular dichroism spectroscopic studies and complexes with the enantiomers of 1-arethyl ammonium salts |
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| Institution: | 1. Department of Pharmaceutical Science & Technology, College of Chemistry and Biology, Donghua University, Shanghai 201620, China;2. Shanghai Eastern Hepatobiliary Surgery Hospital, Shanghai 200433, China;1. Department of Applied Chemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China;2. Jiangsu Vocational College of Information Technology, Wuxi 214153, China |
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| Abstract: | Enantiomerically pure chiral crown ethers containing the phenazine unit (R,R)-2–(S,S)-8] were prepared by two types of cyclization reactions. Ligands (R,R)-2, (R,R)-3, (S,S)-4, (R,R)-5, (R,R)-6 and (R,R)-7 were prepared from phenazine-1,9-diol 9 and the appropriate ditosylates (S,S)-10–(S,S)-15 in weak basic conditions with complete inversion of configuration. Ligands (S,S)-2, (S,S)-7 and (S,S)-8, however, were prepared from 1,9-dichlorophenazine 19 and the appropriate diols (S,S)-16–(S,S)-18 in strong basic conditions with retention of configuration. Enantiomeric recognition of most of the chiral ligands with α-(1-naphthyl)ethylammonium perchlorate (NEA) and α-phenylethylammonium perchlorate (PEA) has been studied by CD spectroscopy. |
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