Highly Enantioselective Iridium-Catalyzed Hydrogenation of Heteroaromatic Compounds, Quinolines

The highly enantioselective hydrogenation of quinoline derivatives is developed using [Ir(COD)Cl]2/(R)-MeO-Biphep/I2 system, and this methodology has been applied to the asymmetric synthesis of three naturally occurring alkaloids angustureine, galipinine, and cuspareine. This method provided an effi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2003-09, Vol.125 (35), p.10536-10537
Main Authors: Wang, Wen-Bo, Lu, Sheng-Mei, Yang, Peng-Yu, Han, Xiu-Wen, Zhou, Yong-Gui
Format: Article
Language:English
Subjects:
Catalysis
Chemical reactivity
Chemistry
Exact sciences and technology
Hydrogenation
Iridium - chemistry
Organic chemistry
Organometallic Compounds - chemistry
Quinolines - chemical synthesis
Quinolines - chemistry
Reactivity and mechanisms
Stereoisomerism
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Summary:The highly enantioselective hydrogenation of quinoline derivatives is developed using [Ir(COD)Cl]2/(R)-MeO-Biphep/I2 system, and this methodology has been applied to the asymmetric synthesis of three naturally occurring alkaloids angustureine, galipinine, and cuspareine. This method provided an efficient access to a variety of optically active tetrahydroquinolines with up to 96% ee.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0353762