Copper-Catalyzed Intermolecular [4 + 2] Annulation
Enabled by Internal Oxidant-Promoted C(sp<sup>3</sup>)–H Functionalization:
Access to 3‑Trifluoromethylated 3‑Hydroxy-cyclohexan-1-ones
Chuanle Zhu
Hao Zeng
Chi Liu
Fulin Chen
Huanfeng Jiang
10.1021/acs.orglett.9b01817.s001
https://acs.figshare.com/articles/journal_contribution/Copper-Catalyzed_Intermolecular_4_2_Annulation_Enabled_by_Internal_Oxidant-Promoted_C_sp_sup_3_sup_H_Functionalization_Access_to_3_Trifluoromethylated_3_Hydroxy-cyclohexan-1-ones/8263775
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(sp<sup>3</sup>)–H bond by an internal oxdative
C(sp<sup>3</sup>)–H functionalization strategy. Preliminary
investigations revealed that α,β-unsaturated ketoxime
acetates were an internal oxidant, and the <i>in situ</i> generated H<sub>2</sub>O served as the O-source of the carbonyl
oxygen in the product.
2019-06-12 14:46:47
diastereoselective
carbonyl
3- trifluoromethylated 3- hydroxy-cylcohexan -1-ones
Annulation
Access
Internal
Hydroxy-cyclohexan
Functionalization
Trifluoromethylated
Copper-Catalyzed
ketone
strategy
investigation
functionalization
acidic
Oxidant-Promoted
O-source
H 2 O
Preliminary
Enabled
oxidant
cyclolization
copper-catalyzed
oxdative
ketoxime acetates
Intermolecular
bond