- Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
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Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.
- Daniliuc, Constantin,Glorius, Frank,Hu, Tianjiao,Lückemeier, Lukas
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supporting information
p. 23193 - 23196
(2021/09/25)
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- Synthesis of 7-Methyl-1,2-dihydroquinolin-2-ones as Angiotensin II Receptor Antagonists
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A number of biphenyl substituted 1,2-dihydroquinolin-2-ones were synthesized by regiospecific alkylation of the corresponding 1H-derivatives.Again, these precursors were prepared in three steps by acetoacetylation of anilines, regiospecific C-alkylation of the resulting β-ketoanilides and subsequent condensation to the quinolines.One of the target compounds, 2--1,2-dihydroquinolin-3-yl>-N,N-dimethylacetamide (10e), is a potent angiotensin II receptor antagonist.
- Beier, Norbert,Labitzke, Erwin,Mederski, Werner W.K.R.,Radunz, Hans-Eckart,Rauschenbach-Ruess, Karin,Schneider, Bjoern
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p. 117 - 132
(2007/10/02)
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