Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines via SNAr,Chemical Communications

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Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines via SNAr
Chemical Communications ( IF 4.3 ) Pub Date : 2021-09-06 , DOI: 10.1039/d1cc04335h
Mariel M Cardenas ₁ , Mirza A Saputra ₁ , Deane A Gordon ₁ , Andrea N Sanchez ₁ , Nobuyuki Yamamoto ₁ , Jeffrey L Gustafson ₁

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Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines via the nucleophilic aromatic substitution (S_NAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceeded via DKR while higher barrier substrates proceeded via KR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.

中文翻译：

通过 SNAr 催化对转选择性动态动力学拆分和 3-芳基喹啉动力学拆分

在此，我们报道了通过催化量的金鸡纳生物碱衍生的脲介导的苯硫酚亲核芳香取代（S _N Ar）成3-芳基-2-氟喹啉，催化对药学相关的3-芳基喹啉的催化选择性合成。这些反应显示出一系列动态动力学拆分 (DKR) 和动力学拆分 (KR) 特征，具体取决于起始材料的立体化学稳定性。低阻隔基材通过DKR 进行，而高阻隔基材则通过KR 进行。另一方面，具有中等稳定性的底物显示出 DKR 和 KR 的特征。最后，我们还表明，我们可以将富含阻转异构体的喹啉功能化为具有药学优势的支架，并且观察到的外消旋作用最少。

更新日期：2021-09-13

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