College of Pharmaceutics and Material Engineering, Jinhua College of Profession and Technology, Jinhua 321007, China
Abstract:
A novel DABCO-catalyzed Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates 3 with dienophiles 4 was developed in the presence of an excess TMSCl and DBU with 1% hydroquinone as polymerization inhibitor in acetonitrile at refluxing temperature under air. This protocol gave cyclic a,b-unsaturated carboxylic acids 5 with complete regioselectivity.