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Novel supramolecular organocatalysts of hydroxyprolinamide based on calix[4]arene scaffold for the enantioselective Biginelli reaction

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Abstract

A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supramolecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.

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Authors and Affiliations

  1. Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, 213164, China

    ZhengYi Li, HuaiJie Xing & XiaoQiang Sun

  2. Institute of Chemical Biology and Drug Innovation, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China

    GuoLi Huang, JuLi Jiang & LeYong Wang

Authors
  1. ZhengYi Li
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  2. HuaiJie Xing
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  3. GuoLi Huang
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  4. XiaoQiang Sun
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  5. JuLi Jiang
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  6. LeYong Wang
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Correspondence to XiaoQiang Sun or JuLi Jiang.

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Li, Z., Xing, H., Huang, G. et al. Novel supramolecular organocatalysts of hydroxyprolinamide based on calix[4]arene scaffold for the enantioselective Biginelli reaction. Sci. China Chem. 54, 1726–1734 (2011). https://doi.org/10.1007/s11426-011-4374-z

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  • DOI: https://doi.org/10.1007/s11426-011-4374-z

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