Asymmetric Michael addition reactions catalyzed by a novel upper-rim functionalized calix[4]squaramide organocatalyst
Asymmetric Michael addition reactions catalyzed by a novel upper-rim functionalized calix[4]squaramide organocatalyst
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DOI：
10.1016/j.cclet.2020.02.057
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发表时间：
2020-02
影响因子：
9.1
通讯作者：
Ke-Fang Yang;Zhiyan Ma;Hong-Xiao Tong;Xiao-qiang Sun;Xiao‐Yu Hu;Zhengyi Li
中科院分区：
文献类型：
--
作者：
Ke-Fang Yang;Zhiyan Ma;Hong-Xiao Tong;Xiao-qiang Sun;Xiao‐Yu Hu;Zhengyi Li
设计并制备了一种新型的上缘功能化杯状[4]方酰胺有机催化剂，该催化剂以双方酰胺和环己二胺为支架，催化一系列1,3-二羰基化合物与α，β-不饱和羰基化合物的不对称Michael加成反应，收率高（99%），对映体过量高（99%ee）。对比实验表明，杯芳烃空腔与手性催化中心在杯芳烃方酰胺催化剂上的协同作用可促进上述反应。此外，该策略还为获得手性铬、萘醌和乙酰丙酮衍生物提供了有价值和容易的途径，这些衍生物是生物和药物化合物的重要骨架。
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 toα,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.