Achiral Counteranion-Induced Reversal of Enantioselectivity in Ni(II)-Catalyzed Friedel–Crafts Alkylation/Annulation of 2-NaphtholsClick to copy article linkArticle link copied!
- Chen-Ying HouChen-Ying HouState Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, ChinaMore by Chen-Ying Hou
- Chun YangChun YangState Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, ChinaMore by Chun Yang
- Yin Tian*Yin Tian*Email: [email protected]State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaMore by Yin Tian
- Ming-Sheng Xie*Ming-Sheng Xie*Email: [email protected]State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, ChinaMore by Ming-Sheng Xie
- Hai-Ming Guo*Hai-Ming Guo*Email: [email protected]State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, ChinaMore by Hai-Ming Guo
Abstract
An achiral counteranion-induced reversal of enantioselectivity in Ni(II)-catalyzed Friedel–Crafts alkylation/annulation of 2-naphthols with β,γ-unsaturated α-keto esters was achieved. Using imidazolidine pyrroloimidazolone pyridine as the ligand and Ni(acac)2 as the Lewis acid, diverse naphthopyran derivatives were obtained in good yields (up to 94% yield) and high enantioselectivities (up to 99% ee). In the presence of Ni(OTf)2 as the Lewis acid, a series of chiral naphthopyran derivatives were obtained in good yields and with a controlled switch in stereoselectivity. DFT calculations reveal that the achiral counteranions regulate H-bonding interactions between counteranions with the N–H of the ligand and the O–H of 2-naphthol.
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