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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
Yang ZP(杨泽鹏); Wu QF(武庆锋); Shao W(邵稳); You SL(游书力)
2015
发表期刊J. Am. Chem. Soc.
卷号137期号:50页码:15899-15906
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.
文章类型论文
学科领域金属有机化学
DOI10.1021/jacs.5b10440
URL查看原文
收录类别SCI
语种英语
WOS记录号WOS:000367562800049
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被引频次:52[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/39682
专题金属有机化学国家重点实验室
通讯作者You SL(游书力)
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
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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.
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