Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones,Angewandte Chemie International Edition

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Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-08-30 , DOI: 10.1002/anie.202108503
Tianjiao Hu ₁ , Lukas Lückemeier ₁ , Constantin Daniliuc ₁ , Frank Glorius ₁

Affiliation

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.

中文翻译：

Ru-NHC 催化 2-喹诺酮不对称氢化成手性 3,4-二氢-2-喹诺酮

不饱和化合物的直接对映选择性氢化产生手性三维图案是合成化学中最直接和最重要的方法之一。我们在温和的反应条件下实现了Ru(II)-NHC催化的2-喹诺酮类药物的不对称氢化。以高产率获得烷基、芳基和卤素取代的光学活性二氢-2-喹诺酮类化合物，并具有中等至优异的对映选择性。该反应为构建简单的手性 3,4-二氢-2-喹诺酮类化合物提供了一种高效且原子经济的途径。所需产物可进一步还原为四氢喹啉和八氢喹诺酮。

更新日期：2021-10-12

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