This study explores the asymmetric FriedelÀ Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones using a squaramide organocatalyst. The squaramide organocatalyst efficiently promoted the asymmetric FriedelÀ Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones, affording the corresponding products bearing both indole motif and trifluoromethyl group in high yields with excellent enantioselectivities (up to 99% ee). The transformation of the obtained adduct to chiral spiro indoline 3-one was also demonstrated.[a] K.