Asymmetric Michael addition reactions catalyzed by a novel upper-rim functionalized calix[4]squaramide organocatalyst |
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| Institution: | 1. Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China;2. College of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 211100, China;1. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, East China University of Science and Technology, Shanghai 200237, China;2. Shanghai Key Laboratory of Chemistry Biology, East China University of Science and Technology, Shanghai 200237, China;1. College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, China;2. School of Life Sciences and Chemistry, Hunan University of Technology, Zhuzhou 412007, China;3. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, China;1. College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China;2. College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China;3. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, 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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