Pincer iridium(III)-catalyzed enantioselective C(sp3)-H functionalization via carbenoid C H insertion of 3-diazooxindoles with 1,4-cyclohexadiene

Autor:	Yanyan Zhu, Xiaoyan Yang, Nan Li, Jun-Fang Gong, Fang Wang, Mao-Ping Song
Rok vydání:	2022
Předmět:	Reaction mechanism chemistry.chemical_compound Chemistry Functional group Enantioselective synthesis chemistry.chemical_element Density functional theory General Chemistry Iridium Carbenoid Medicinal chemistry Catalysis Pincer movement
Zdroj:	Chinese Chemical Letters. 33:2437-2441
ISSN:	1001-8417
Popis:	The asymmetric carbenoid C-H insertion of 3-diazooxindoles into 1,4-cyclohexadiene has been accomplished in the presence of chiral bis-(imidazoline) NCN pincer iridium(III) complexes as the catalysts. With a catalyst loading of 0.5 mol%, the reactions proceeded smoothly at 0 °C to afford a variety of chiral 3-substituted oxindoles in good yields with moderate to excellent enantioselectivities (up to 99% ee). The protocol exhibits good functional group tolerance with respect to 3-diazooxindoles and is readily scaled up to 2 mmol scale without any loss in activity and enantioselectivity. Density functional theory (DFT) calculations have been performed to better understand the reaction mechanism and to explain the stereochemical outcome of the reactions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0990aef48eefc9a8979214bddadb753d https://doi.org/10.1016/j.cclet.2021.11.067 Zobrazit plný text záznamu Full Text from ScienceDirect