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Copper-Catalyzed Intermolecular [4 + 2] Annulation Enabled by Internal Oxidant-Promoted C(sp3)–H Functionalization: Access to 3‑Trifluoromethylated 3‑Hydroxy-cyclohexan-1-ones
journal contribution
posted on 2019-06-12, 14:46 authored by Chuanle Zhu, Hao Zeng, Chi Liu, Fulin Chen, Huanfeng JiangA copper-catalyzed
diastereoselective [4 + 2] cyclolization of
α,β-unsaturated ketoxime acetates and trifluoromethyl
ketones affords various 3-trifluoromethylated 3-hydroxy-cylcohexan-1-ones
smoothly. This reaction features the selective functionalization of
a less acidic C(sp3)–H bond by an internal oxdative
C(sp3)–H functionalization strategy. Preliminary
investigations revealed that α,β-unsaturated ketoxime
acetates were an internal oxidant, and the in situ generated H2O served as the O-source of the carbonyl
oxygen in the product.
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diastereoselectivecarbonyl3- trifluoromethylated 3- hydroxy-cylcohexan -1-onesAnnulationAccessInternalHydroxy-cyclohexanFunctionalizationTrifluoromethylatedCopper-CatalyzedketonestrategyinvestigationfunctionalizationacidicOxidant-PromotedO-sourceH 2 OPreliminaryEnabledoxidantcyclolizationcopper-catalyzedoxdativeketoxime acetatesIntermolecularbond
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