Enantioselective Cu-Catalyzed Nucleophilic Addition of Fluorinated Reagents: C–C Bond Formation for the Synthesis of Chiral Vicinal Difluorides
2022
Lin, Huaxin | Jiao, Wei | Chen, Zhiwei | Han, Jian | Fang, Dongmei | Wang, Min | Miao Tsan,
Herein we described the first enantioselective Cu/sulfoxide phosphine (SOP) complex catalyzed nucleophilic addition of fluorinated enolates to gem-difluoroalkenes. The enantioenriched vicinal difluorides, containing a chiral tertiary fluoride and a fluoroalkene, were successfully afforded via C–C bond formation in good yields (up to 94% yield), high Z/E-selectivity (5:1 → 50:1 for Z-isomer), and excellent enantioselectivities (up to 98.5:1.5 er). Utility of this approach was demonstrated by modification of complex biologically active compounds.
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