Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Iridium-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Hydroxyquinolines: Simultaneous Weakening of the Aromaticity of Two Consecutive Aromatic Rings

Iridium-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Hydroxyquinolines: Simultaneous Weakening of the Aromaticity of Two Consecutive Aromatic Rings
Shu-Li You, Ze-Peng Yang, Chao Zheng, Ru Jiang
Intramolecular asymmetric allylic alkylation reactions of 5- and 7-hydroxyquinoline derivatives were realized by a chiral Ir/NHC catalyst. A series of functionalized cyclic enones were afforded in excellent yields (up to 99%) and high enantioselectivity (up to 97% ee). Theoretical computations revealed that the aromaticity of the two consecutive rings of hydroxyquinoline substrates is significantly weakened. A highly efficient formal synthesis of (−)-gephyrotoxin was accomplished based on this method.

Publisher URL: http://dx.doi.org/10.1021/jacs.8b00136

DOI: 10.1021/jacs.8b00136

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