Enantioselective Cu-Catalyzed Nucleophilic Addition of Fluorinated Reagents: C–C Bond Formation for the Synthesis of Chiral Vicinal Difluorides

作者：Huaxin Lin, Wei Jiao, Zhiwei Chen, Jian Han, Dongmei Fang, Min Wang, Jian Liao · 发表于：Organic Letters · 年份：2022 · DOI：10.1021/acs.orglett.2c00518 · 被引用次数：29 · 研究领域：Fluorine in Organic Chemistry、Catalytic C–H Functionalization Methods、Asymmetric Synthesis and Catalysis

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.