دورية
Achiral Counteranion-Induced Reversal of Enantioselectivity in Ni(II)-Catalyzed Friedel–Crafts Alkylation/Annulation of 2-Naphthols
| العنوان: | Achiral Counteranion-Induced Reversal of Enantioselectivity in Ni(II)-Catalyzed Friedel–Crafts Alkylation/Annulation of 2-Naphthols |
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| المؤلفون: | Hou, Chen-Ying, Yang, Chun, Tian, Yin, Xie, Ming-Sheng, Guo, Hai-Ming |
| المصدر: | Organic Letters; August 2024, Vol. 26 Issue: 30 p6390-6395, 6p |
| مستخلص: | 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)2as 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)2as 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. |
| قاعدة البيانات: | Supplemental Index |
Find this issue from the American Chemical Society | تدمد: | 15237060 15237052 |
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| DOI: | 10.1021/acs.orglett.4c02156 |