Copper-Catalyzed Intermolecular [4 + 2] Annulation
Enabled by Internal Oxidant-Promoted C(sp3)–H Functionalization:
Access to 3‑Trifluoromethylated 3‑Hydroxy-cyclohexan-1-ones
Posted on 2019-06-12 - 14:46
A 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.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Zhu, Chuanle; Zeng, Hao; Liu, Chi; Chen, Fulin; Jiang, Huanfeng (2019). Copper-Catalyzed Intermolecular [4 + 2] Annulation
Enabled by Internal Oxidant-Promoted C(sp3)–H Functionalization:
Access to 3‑Trifluoromethylated 3‑Hydroxy-cyclohexan-1-ones. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b01817
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
AUTHORS (5)
CZ
Chuanle Zhu
HZ
Hao Zeng
CL
Chi Liu
FC
Fulin Chen
HJ
Huanfeng Jiang
KEYWORDS
diastereoselectivecarbonyl3- trifluoromethylated 3- hydroxy-cylcohexan -1-onesAnnulationAccessInternalHydroxy-cyclohexanFunctionalizationTrifluoromethylatedCopper-CatalyzedketonestrategyinvestigationfunctionalizationacidicOxidant-PromotedO-sourceH 2 OPreliminaryEnabledoxidantcyclolizationcopper-catalyzedoxdativeketoxime acetatesIntermolecularbond