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

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作者：

机构：

[1] Yang, Ze-Peng

[2] Wu, Qing-Feng

[3] Shao, Wen

[4] You, Shu-Li

来源：

You, Shu-Li (slyou@sioc.ac.cn) | 1600年 / American Chemical Society卷 / 137期

关键词：

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. © 2015 American Chemical Society;

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Journal article (JA)

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