132162-30-2Relevant academic research and scientific papers
Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
Daniliuc, Constantin,Glorius, Frank,Hu, Tianjiao,Lückemeier, Lukas
, p. 23193 - 23196 (2021/09/25)
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.
Nickel-Catalyzed Enantioselective Carbamoyl Iodination: A Surrogate for Carbamoyl Iodides
Abel-Snape, Xavier,Glorius, Frank,Lautens, Mark,Marchese, Austin D.,Mirabi, Bijan,Whyte, Andrew,Wollenburg, Marco
, p. 4780 - 4785 (2020/05/19)
This work reports the enantioselective formal transfer of a carbamoyl iodide across a 1,1-disubstituted styrene using Ni-catalysis. Employing an air-stable Ni(II) precatalyst and a commercially available chiral ligand ((S)-tBuPHOX), enantioenriched 3,3-disubstituted iodooxindoles were obtained in up to 90% yield and up to 97:3 e.r. This methodology was applied to the total synthesis of (-)-esermethole and (-)-phenserine.
Novel synthesis and cytotoxic activity of 1,4-disubstituted 3-methylidene-3,4-dihydroquinolin-2(1H)-ones
Pi?ta, Marlena,K?dzia, Jacek,Janecka, Anna,Pomorska, Dorota K.,Rózalski, Marek,Krajewska, Urszula,Janecki, Tomasz
, p. 78324 - 78335 (2015/09/28)
A novel, efficient synthesis of 1,4-disubstituted 3-methylidene-3,4-dihydrodihydroquinolin-2(1H)-ones was accomplished via a three step reaction sequence comprising N-alkylation of 3-diethoxyphosphorylquinolin-2(1H)-one, Michael addition of various Grignard reagents to N-alkylated 3-diethoxyphosphorylquinolin-2(1H)-ones and a Horner-Wadsworth-Emmons reaction of the obtained adducts with formaldehyde. Effective synthesis of the starting 3-diethoxyphosphorylquinolin-2(1H)-one was also developed. Furthermore, the obtained 3-methylidene-3,4-dihydroquinolin-2(1H)-ones were evaluated for their cytotoxic activity.
