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Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 7: 1531 - 1536

DOI: https://doi.org/10.6023/cjoc201502018

Notes

Synthesis of Calix[4]proline Derivatives and Their Chiral Recognition for Enantiomers of Mandelic Acid

  • Li Zhengyi ,
  • Zhou Kun ,
  • Lai Yuan ,
  • Sun Xiaoqiang ,
  • Wang Leyong
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  • a Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164;
    b Laboratory for Supramolecular Chemistry and Dynamic Materials, School of Chemistry and Chemical Engineering, Nanjing Universty, Nanjing 210093

Received date: 2015-02-10

  Revised date: 2015-03-02

  Online published: 2015-03-19

Supported by

Project supported by the NSFC (No. 21002009), Major Program for the Natural Science Research of Jiangsu Colleges and Universities (Nos. 12KJA150002, 14KJA150002), Priority Academic Program Development of Jiangsu Higher Education Institution (PAPD), and Qing Lan Project of Jiangsu Province.

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Abstract

Five chiral calix[4]proline derivatives were designed and synthesized from aminocalix[4]arenes, and their structures were characterized by 1H NMR, 13C NMR, IR, ESI-MS and elemental analysis. The chiral recognition ability for enantiomers of mandelic acid was investigated by NMR techniques, and the results showed that 5,11-diprolinamides substituted calix[4]arene 2b could well and selectively recognize the two enantiomers of mandelic acid (KL/KD≈94). A possible recognition mechanism was proposed, which was constructed by cooperative multi-supramolecular interactions including intermolecular acid-base, hydrogen bond and π···π stacking interactions.

Key words： calix[4]arene; L-proline; mandelic acid; chiral recognition; NMR

Cite this article

Li Zhengyi , Zhou Kun , Lai Yuan , Sun Xiaoqiang , Wang Leyong . Synthesis of Calix[4]proline Derivatives and Their Chiral Recognition for Enantiomers of Mandelic Acid[J]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1531 -1536 . DOI: 10.6023/cjoc201502018

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