Asymmetric Michael addition reactions catalyzed by a novel upper-rim functionalized calix[4]squaramide organocatalyst |
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Authors: | Ke Yang Zhiyan Ma Hong-Xiao Tong Xiao-Qiang Sun Xiao-Yu Hu Zheng-Yi Li |
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Institution: | Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China; College of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 211100, China |
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Abstract: | A novel upper-rim functionalized calix4]squaramide organocatalyst bearing bis-squaramide and cyclohexanediamine scaffolds was designed and prepared to catalyse a serial of asymmetric Michael addition of 1,3-dicarbonyl compounds to α,β-unsaturated carbonyl compounds in high yields (up to 99 %) and good to excellent enantiomeric excesses (up to 99% ee). The comparative experiments indicated that the cooperative effect between calixarenes cavitives and chiral catalytic centers on this calix4]squaramide catalyst could promote these reactions. Moreover, this strategy also provides valuable and easy access to chiral chromene, naphthoquinone and acetylacetone derivatives, which are important skeletons in biological and pharmaceutical compounds. |
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Keywords: | Calix[4]squaramide Supramolecular catalyst Asymmetric catalysis Michael addition Organic synthesis |
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