Cui Liying, Yang Xiaofeng, Yuan Changchun, Zhou Zhenghong
School of Chemistry and Chemical Engineering, North University of China, Taiyuan 030051, P.R. China.
Institute and State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, P. R. China.
J Org Chem. 2024 Dec 20;89(24):17950-17959. doi: 10.1021/acs.joc.4c01327. Epub 2024 Dec 10.
An asymmetric tandem esterification/Michael addition reaction of β-keto acylpyrazoles with -hydroxychalcones has been established under the catalysis of a bifunctional squaramide-tertiary amine. A wide variety of biorelevant 3,4-dihydrocoumarin derivatives were generally obtained in high yields (up to 93%) with excellent diastereo- and enantioselectivities (>19:1 dr, up to 93% ee) under mild reaction conditions. This reaction represents the successful application of β-keto acylpyrazoles as 2C building blocks in catalytic asymmetric cyclizations.
在双功能方酰胺-叔胺的催化下，实现了β-酮酰基吡唑与α-羟基查尔酮的不对称串联酯化/Michael加成反应。在温和的反应条件下，通常可以高产率（高达93%）获得各种具有生物相关性的3,4-二氢香豆素衍生物，且具有优异的非对映选择性和对映选择性（非对映体比例>19:1，对映体过量高达93%）。该反应代表了β-酮酰基吡唑作为2C结构单元在催化不对称环化反应中的成功应用。
