Ring-expanded chiral rhombamine macrocycles for efficient NMR enantiodiscrimination of carboxylic acid derivatives |
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| Institution: | 1. Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering and High Technology Research Center, Kansai University, Suita, Osaka 564-8680, Japan;2. Graduate School of Human and Environmental Studies, Kyoto Univesity, Kyoto 606-8501, Japan;1. Key Laboratory of Eco-Environment-Related Polymer Materials of Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, Key Laboratory of Bioelectrochemistry & Environmental Analysis of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, PR China;2. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China;3. Gansu Computing Center, Lanzhou 730030, PR China;1. School of Chemical and Pharmaceutical Engineering, Sichuan University of Science & Engineering, Zigong 643000, PR China;2. Key Laboratory of Green Catalysis of Sichuan Institute of High Education, Zigong 643000, PR China;1. Department of Organic Technology, Kaunas University of Technology, Radvilenu Plentas 19, 50254 Kaunas, Lithuania;2. Lviv Polytechnic National University, S. Bandery Str. 12, 79013 Lviv, Ukraine |
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| Abstract: | Novel 46-membered chiral rhombamine macrocycles (R,R,R,R)-8a and 8b were synthesized by 2+2] cyclocondensation reactions of (R,R)-1,2-diaminocyclohexane with the corresponding dialdehydes and subsequent reduction with NaBH4. The X-ray crystal structure of 1:4 dioxane complex with (R,R,R,R)-8a indicated a rhombus conformation of the chiral macrocycle. Compounds (R,R,R,R)-8a and 8b were tested as chiral shift reagents for a wide range of α-substituted carboxylic acids and amino acid derivatives. Enantiodiscrimination of 1H NMR signals was observed with ΔΔδ values of up to 0.214 ppm. |
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