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Herein we report a chiral phosphoric acid-catalyzed intermolecular C2 Friedel-Crafts alkylation reaction between ortho-alkynylnaphthols and various 3-substituted indoles, affording axially chiral alkenes with up to 93% yields (E/Z 201) and up to 98% ee under mild reaction condition. Other substituted indole derivatives could be also tolerated in this system, giving the corresponding axially chiral alkenes with high yields and in excellent enantioselectivity.The 111 reaction of DyCl3·6H2O, K3[CCN)6] and bpyO2 in H2O has provided