Unified Enantioselective Allylations and Vinylogous Reactions Enabled by Visible Light-Driven Chiral Lewis Acid Catalysis

In contemporary organic synthesis, chemists actively pursue a diverse range of substrates that can be efficiently catalyzed within an integrated system, playing a crucial role in advancing the pharmaceutical industry. However, due to the influence of substituents on reactivity and selectivity, it poses a challenging dilemma to explore different strategies for activating substrates with distinct functional groups. Herein, we have developed an important visible light-driven chiral Lewis acid catalysis platform which facilitates the unified allylations and vinylogous reactions of various allyl bromides and isatins for the highly enantio- and diastereoselective construction of valuable 3-allyl-3-hydroxy oxindoles. The success of this approach lies in utilizing a radical pathway for intermediate formation and stereocenter generation. Moreover, the activation capability of chiral Lewis acids provides an opportunity to achieve sufficient enantiocontrol and enhance regioselectivity. The robustness of this method is demonstrated by its application in precise radical-based propargylation reactions using readily accessible propargyl bromides.