Gold Catalysis, Asymmetric Friedel–Crafts Alkylation Cascade for One-Pot Synthesis of Chiral Dihydrocarbazoles and Dihydrodibenzofurans

A one-pot gold-catalyzed acyl migration followed by ytterbium-catalyzed asymmetric Friedel–Crafts alkylation is disclosed, leading to the rapid synthesis of chiral dihydrocarbazoles and dihydrodibenzofuran in generally moderate to good overall yields with good to excellent enantioselectivities. The gold-catalyzed acyl migration of propargyl acetates generates α-ylidene-β-diketones with high E/Z ratios, which are then subjected to the ytterbium-catalyzed asymmetric Friedel–Crafts alkylation without any purification. Importantly, this protocol provides a new type of substrate for asymmetric Friedel–Crafts alkylation.