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学科主题: 金属有机化学
题名: Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines
其他题名: 铱催化吡啶、吡嗪、喹啉和异喹啉的分子内不对称烯丙基芳反应
作者: Yang ZP(杨泽鹏); Wu QF(武庆锋); Shao W(邵稳); You SL(游书力)
通讯作者: 游书力
刊名: J. Am. Chem. Soc.
发表日期: 2015
DOI: 10.1021/jacs.5b10440
卷: 137, 期:50, 页:15899-15906
收录类别: SCI
文章类型: 论文
英文摘要: The first Ir-catalyzed intramolecular asymmetric allylic dearomatization reaction of pyridines, pyrazines, quinolines, and isoquinolines has been developed. Enabled by in situ formed chiral Ir-catalyst, the dearomatized products were isolated in high levels of yield (up to 99% yield) and enantioselectivity (up to 99% ee). It is worth noting that the Me-THQphos ligand is much more efficient than other tested ligands for the dearomatization of pyrazines and certain quinolines. Mechanistic studies of the dearomatization reaction were carried out, and the results suggest the feasibility of an alternative process which features the formation of a quinolinium as the key intermediate. The mechanistic findings render this reaction a yet unknown type in the chemistry of Reissert-type reactions. In addition, the utility of this method was showcased by a large-scale reaction and formal synthesis of (+)-gephyrotoxin.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000367562800049
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39682
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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作者单位: 中科院上海有机化学研究所, 金属有机化学国家重点实验室

Recommended Citation:
Yang ZP,Wu QF,Shao W,et al. Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines[J]. J. Am. Chem. Soc.,2015,137(50):15899-15906.
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