Asymmetric Friedel–Crafts Alkylation Reaction in the Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters

Abstract

Construction of all-carbon quaternary stereocenter by asymmetric Friedel–Crafts alkylation reaction remains a significant challenge. By the introduction of CF₃ group at the β-position of nitroalkene, a highly enantioselective Friedel–Crafts reaction of indoles with β-CF₃-β-substituted nitroalkenes was achieved using Ni(ClO₄)₂-bisoxazoline complex as a catalyst, which afforded indole-bearing chiral compounds with trifluoromethylated all-carbon quaternary stereogenic centers in good yields and excellent enantio­selectivities.

Key words

alkylation - asymmetric catalysis - fluorine - indole - nickel

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