title: Catalytic Enantioselective γ-Selective Additions of 2-Allylazaarenes to Activated Ketones.
abstract: Reported herein is the first example of 2-allylazaarenes in asymmetric catalysis. Highly γ-selective allylation was demonstrated for activated ketones, including isatins and trifluoromethyl ketones. In the presence of either an amino-acid-based tertiary amine or quaternary ammonium salt catalyst, two series of tertiary hydroxy-containing moieties were installed at the remote δ-position of azaarenes in good chemical yields, excellent enantioselectivities, and E/Z ratios. The success of current γ-selective reactions should provide inspiration for expansion to other allylazaarene derivatives and would open up new paradigms for the synthesis of chiral γ- and/or δ-functionalized azaarenes.
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P.R. China.
authors.forename: Xiangbin
authors.initials: X
authors.lastname: Bai
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P.R. China.
authors.forename: Guangkuo
authors.initials: G
authors.lastname: Zeng
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P.R. China.
authors.forename: Tianju
authors.initials: T
authors.lastname: Shao
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P.R. China.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
keywords: allylic compounds; arenes; heterocycles; organocatalysis; synthetic methods