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  • Title: Highly enantioselective construction of trifluoromethylated all-carbon quaternary stereocenters via nickel-catalyzed Friedel-Crafts alkylation reaction.
    Author: Gao JR, Wu H, Xiang B, Yu WB, Han L, Jia YX.
    Journal: J Am Chem Soc; 2013 Feb 27; 135(8):2983-6. PubMed ID: 23409797.
    Abstract:
    A highly enantioselective Friedel-Crafts alkylation reaction of indoles with β-CF(3)-β-disubstituted nitroalkenes was achieved using a Ni(ClO(4))(2)-bisoxazoline complex as a catalyst, which afforded indole-bearing chiral compounds with trifluoromethylated all-carbon quaternary stereocenters in good yields with excellent enantioselectivities (up to 97% ee). The transformation of one of the products into first a trifluoromethylated tryptamine and then a trifluoromethylated tetrahydro-β-carboline by sequential nitro reduction and Pictet-Spengler cyclization were realized with complete preservation of enantiopurity.
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