Wang Qiang, Pan Ya-Lin, Liang Ren-Xiao, Hu Yuan-Yuan, Jia Yi-Xia
College of Chemical Engineering, State Key Laboratory Breeding Base of Green Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou, 310014, China.
School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin, 300384, China.
Org Biomol Chem. 2025 Jan 29;23(5):1073-1077. doi: 10.1039/d4ob01881h.
Herein, we report an enantioselective Pd/Cu-catalyzed sequential Heck/Sonogashira coupling reaction of electron-rich enamides with terminal alkynes as substrates. This transformation proceeds smoothly to afford 3-propargyl isoindolinone derivatives bearing quaternary stereogenic centers in moderate to good yields (43-77% yield) and good to excellent enantioselectivity (up to 93% ee). Functional groups such as halogen atoms (F, Cl, and Br), thienyl, and silyl moieties are tolerated well. Synthetic transformations of the 3-propargyl isoindolinone product show the utility value of the reaction.
