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Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines
Alternative Title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
Source PublicationJ. Am. Chem. Soc.
Volume137Issue:50Pages:15899-15906
AbstractThe 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.
Subtype论文
Subject Area金属有机化学
DOI10.1021/jacs.5b10440
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000367562800049
Citation statistics
Cited Times:65[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39682
Collection金属有机化学国家重点实验室
Corresponding AuthorYou SL(游书力)
Affiliation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
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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