Ruthenium-catalyzed enantioselective propargylation of l-(triisopropylsilyl)-1H-indoles with propargylicalcohols gives the corresponding β-propargylated indoles in good yields with high enantioselectivity. Reactions with l-(l-naphthyl)prop-2-yn-l-ol achieve the highest enantioselectivity (up to 95% ee).