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Unprecedented synthesis of chiral calix[4](aza)crowns and its potent encapsulating methanol

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Abstract

Unprecedented synthesis of chiral (aza)crown ethers of calix[4]arene derivatives bearing a carboxyl amide bridge was described. The synthesis proceeds through condensation of the corresponding dinitriles with optically active 1,2-aminoalcohols, and is catalyzed by the ZnCl2 Lewis acid at elevated temperature in a very efficient one-pot process. The cavity of calix[4](aza)crowns can encapsulate methanol molecules by O-H⋯п interaction, which has been confirmed by X-ray crystal structures and ESI-MS.

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Authors and Affiliations

  1. Key Laboratory of Mesoscopic Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China

    ZhengYi Li, MingYu Teng, JieJie Ma, Ji Huang, LeYong Wang & Yi Pan

  2. Xuzhou Medical College, Xuzhou, 221004, China

    ZhengYi Li

Authors
  1. ZhengYi Li
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  2. MingYu Teng
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  3. JieJie Ma
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  4. Ji Huang
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  5. LeYong Wang
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  6. Yi Pan
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Correspondence to LeYong Wang or Yi Pan.

Additional information

Supported by the National Basic Research Program of China (Grant No. 2007CB925103), the National Natural Science Foundation of China (Grant No. 20602017), and NCET-07-0425

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Li, Z., Teng, M., Ma, J. et al. Unprecedented synthesis of chiral calix[4](aza)crowns and its potent encapsulating methanol. Sci. China Ser. B-Chem. 52, 497–504 (2009). https://doi.org/10.1007/s11426-009-0045-8

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  • DOI: https://doi.org/10.1007/s11426-009-0045-8

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