Highly Enantioselective Iridium-Catalyzed Hydrogenation of Heteroaromatic Compounds, Quinolines
Top Cited Papers
- 9 August 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (35) , 10536-10537
- https://doi.org/10.1021/ja0353762
Abstract
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.Keywords
This publication has 13 references indexed in Scilit:
- Hydrogenation of Quinoline by Rhodium Catalysts Modified with the Tripodal Polyphosphine Ligand MeC(CH2PPh2)3Helvetica Chimica Acta, 2001
- Identification of the alkaloids of Galipea officinalis by gas chromatography–mass spectrometryPhytochemical Analysis, 2001
- Transition metal complexes with the C1-symmetric diphosphines (R)-(R)-3-benzyl-2,4-bis(diphenylphosphino)pentane and (R)-(R)-3-benzyl(p-sulphonate)-2,4-bis(diphenylphosphino)pentane sodium salt. Applications to enantioselective catalysis in different phase systemsJournal of Organometallic Chemistry, 2001
- Enantioselective Homogeneous Hydrogenation of Monosubstituted Pyridines and FuransMonatshefte für Chemie / Chemical Monthly, 2000
- Catalytic Asymmetric Hydrogenation of Heteroaromatic Compounds, IndolesJournal of the American Chemical Society, 2000
- Activity Against Mycobacterium tuberculosis of Alkaloid Constituents of Angostura Bark, Galipea officinalisPlanta Medica, 1999
- Planar‐Chiral Ferrocenes: Synthetic Methods and ApplicationsAngewandte Chemie International Edition in English, 1996
- Homogeneous catalytic hydrogenation. 6. Synthetic and mechanistic aspects of the regioselective reductions of model coal nitrogen, sulfur, and oxygen heteroaromatic compounds using the (.eta.5-pentamethylcyclopentadienyl)rhodium tris(acetonitrile) dication complex as the catalyst precursorJournal of the American Chemical Society, 1992
- Reactions of chromium carbene complexes with 1-azirines. Synthesis of N-vinylimidatesOrganometallics, 1985
- Evidence for single electron transfer in the reduction of organic halides by lithium triethylborohydrideThe Journal of Organic Chemistry, 1984