Organocatalytic C_sp2–O Amination of Quinolin-4(1H)-ones with 3-Alkynyl-3-hydroxyisoindolinones

Abstract

The Brønsted acid catalytic C sp2 −O amination of quinolin-4(1H)-ones with 3-alkynyl-3-hydroxyisoindolinones as animation reagents has been developed. The cascade dehydration/conjugate addition/intramolecular annulation/ring-opening reaction proceeded smoothly to afford a broad scope of aminated products with high efficiency. Furthermore, the enantioselective construction of C sp2 −N atropisomers was also investigated in the presence of chiral phosphoric acid. Importantly, this work not only realized the organocatalytic C sp2 −O amination of quinolin-4(1H)-ones but also laid the foundation for directly asymmetric synthesis of C sp2 −N atropisomers.