N-Heterocyclic Carbene/Copper Cooperative Catalysis for the Asymmetric Synthesis of Spirooxindoles.
Zi-Jing ZhangLing ZhangRui-Long GengJin SongXiao-Hua ChenLiu-Zhu GongPublished in: Angewandte Chemie (International ed. in English) (2019)
Highly enantioselective [3+3] and [3+4] annulations of isatin-derived enals with ethynylethylene carbonates and ethynyl benzoxazinanones are enabled by NHC/cooper cooperative catalysis, leading to a big library of spirooxindole derivatives in high structural diversity and enantioselectivity (up to 99 % ee). Both reactions represent a nicely synergistic integration of NHC and copper catalysis, in which both catalysts activate the substrates and the chiral NHC perfectly controls the stereochemistry.