An efficient yttrium(III)-catalyzed highly enantioselective Friedel-Crafts alkylation of β-trichloro(trifluoro)methyl aryl enones is described. The reaction delivered a series of functionalized indoles with a chiral tertiary carbon center bearing a trichloro(trifluoro)methyl group in excellent results (up to 96% ee and 99% yield) under mild conditions.