Organocatalytic Csp2–O Amination of Quinolin-4(1H)-ones with 3-Alkynyl-3-hydroxyisoindolinones

The Brønsted acid catalytic Csp2–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 Csp2–N atropisomers was also investigated in the presence of chiral phosphoric acid. Importantly, this work not only realized the organocatalytic Csp2–O amination of quinolin-4(1H)-ones but also laid the foundation for directly asymmetric synthesis of Csp2–N atropisomers.