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Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines. 2003

Wen-Bo Wang, and Sheng-Mei Lu, and Peng-Yu Yang, and Xiu-Wen Han, and Yong-Gui Zhou
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China.

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.

UI MeSH Term Description Entries
D007495 Iridium A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.
D009942 Organometallic Compounds A class of compounds of the type R-M, where a C atom is joined directly to any other element except H, C, N, O, F, Cl, Br, I, or At. (Grant & Hackh's Chemical Dictionary, 5th ed) Metallo-Organic Compound,Metallo-Organic Compounds,Metalloorganic Compound,Organometallic Compound,Metalloorganic Compounds,Compound, Metallo-Organic,Compound, Metalloorganic,Compound, Organometallic,Compounds, Metallo-Organic,Compounds, Metalloorganic,Compounds, Organometallic,Metallo Organic Compound,Metallo Organic Compounds
D011804 Quinolines
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D006865 Hydrogenation Addition of hydrogen to a compound, especially to an unsaturated fat or fatty acid. (From Stedman, 26th ed) Hydrogenations
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

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