Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines

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	Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines
	Yang ZP(杨泽鹏); Wu QF(武庆锋); Shao W(邵稳); You SL(游书力)
刊名	J. Am. Chem. Soc.
	2015
卷号	137 期号:50 页码:15899-15906
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
通讯作者	游书力
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.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jacs.5b10440
语种	英语
WOS记录号	WOS:000367562800049
内容类型	期刊论文
源URL	[http://ir.sioc.ac.cn/handle/331003/39682]
专题	上海有机化学研究所_金属有机化学国家重点实验室
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
推荐引用方式 GB/T 7714	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.
APA	杨泽鹏,武庆锋,邵稳,&游书力.(2015).Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines.J. Am. Chem. Soc.,137(50),15899-15906.
MLA	杨泽鹏,et al."Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines".J. Am. Chem. Soc. 137.50(2015):15899-15906.