1570194-58-9Relevant academic research and scientific papers
Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of: O -pivaloyl oximes with α-diazo compounds
Chang, Junbiao,Deng, Wei-Qiao,Kong, Lingheng,Li, Xingwei,Liu, Bingxian,Sun, Lincong,Wang, Fen,Zhao, Yanlian
, p. 8268 - 8271 (2021/08/25)
Chiral RhIII catalysts can catalyze the asymmetric [4+1] spiroannulation of O-pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C-H activation and N-O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities. This journal is
Redox-Neutral Access to Isoquinolinones via Rhodium(III)-Catalyzed Annulations of O-Pivaloyl Oximes with Ketenes
Yang, Xifa,Liu, Song,Yu, Songjie,Kong, Lingheng,Lan, Yu,Li, Xingwei
, p. 2698 - 2701 (2018/05/22)
A mild and redox-neutral [4 + 2] annulation of O-pivaloyl oximes with ketenes has been realized for synthesis of quaternary-carbon-stereocenter-containing (QCSC) isoquinolinones, where the N-OPiv not only acts as an oxidizing group but also offers coordination saturation to inhibit protonolysis. The reaction mechanism has been studied by DFT calculations.
Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines
Zhang, Zhi-Wei,Lin, Aijun,Yang, Jiong
, p. 7041 - 7050 (2014/08/18)
Methyl ketone oxime esters have been found to be excellent coupling partners for C(sp2)-C(sp3) bond formation via Pd-catalyzed aromatic C-H activation. This transformation forms the basis of an approach to regioselectively synthesize substituted isoquinolines via coupling with aryloxime esters. Our mechanistic studies suggested that the reaction proceeded through Pd(II)-catalyzed aromatic C-H activation, tautomerization, and a 1,3-shift of the palladacycle-ligated methyl ketone oxime ester to enable the C-C bond formation by reductive elimination, and intramolecular condensation of an imido-Pd(II) intermediate to form the heterocycle. The aryloxime group not only was used as a directing group for Pd-catalyzed aromatic C-H activation but also functioned as an internal oxidant to allow the reaction to be redox-neutral. Our study illuminated the scope and limitations of this C-H alkylation process, which may serve as the point of departure for developing other C-H functionalization reactions using oxime esters and potentially other carbonyl derivatives as the nucleophilic coupling partners.
