Citation: Ke Yang, Zhiyan Ma, Hong-Xiao Tong, Xiao-Qiang Sun, Xiao-Yu Hu, Zheng-Yi Li. Asymmetric Michael addition reactions catalyzed by a novel upper-rim functionalized calix[4]squaramide organocatalyst[J]. Chinese Chemical Letters, ;2020, 31(12): 3259-3262. doi: 10.1016/j.cclet.2020.02.057 shu

Asymmetric Michael addition reactions catalyzed by a novel upper-rim functionalized calix[4]squaramide organocatalyst

Ke Yang ^a ,
Zhiyan Ma ^a ,
Hong-Xiao Tong ^a ,
Xiao-Qiang Sun ^{a, *,} ,
Xiao-Yu Hu ^{a, b} ,
Zheng-Yi Li ^{a, *,}

a.
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
b.
College of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 211100, China

xqsun@cczu.edu.cn

zyli@cczu.edu.cn

Received Date: 6 January 2020
Revised Date: 18 February 2020
Accepted Date: 28 February 2020
Available Online: 29 February 2020

Figures(5)

A novel upper-rim functionalized calix[4]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 calix[4]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.
- Calix[4]squaramide,
- Supramolecular catalyst,
- Asymmetric catalysis,
- Michael addition,
- Organic synthesis
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