Asymmetric synthesis of quinolinone-based polycyclic indoles through [1,3]-rearrangement/cyclization reaction

Abstract

We have developed an enantioselective [1,3]-rearrangement/cyclization reaction that provides efficient access to quinolinone-based polycyclic indole derivatives. This catalytic system exhibits broad substrate scope, enabling the stereocontrolled synthesis of two valuable scaffolds: 3,4-dihydroquinolin-2-ones and cyclopenta[b]indoles with excellent stereoselectivity (>40 examples, 83–99% ee, >19 : 1 dr). Notably, the obtained products demonstrate promising anticancer activity.