Iridium-Catalyzed Intermolecular Asymmetric Allylic Amination with Pyridones,Advanced Synthesis & Catalysis

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Iridium-Catalyzed Intermolecular Asymmetric Allylic Amination with Pyridones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-06-14 , DOI: 10.1002/adsc.202200347
Hang-Fei Tu ₁ , Yu-Han Nie ₁ , Chao Zheng ₁ , Shu-Li You ₁

Affiliation

We report herein a catalytic synthetic method for enantioenriched N-substituted pyridones. By employing chiral iridium catalyst generated from the Carreira [P/olefin] ligand, intermolecular asymmetric allylic amination of allyl alcohols with pyridones proceeded smoothly with excellent chemo-, regio- and enantioselectivities (>19:1 N/O, >19:1 b/l and ≥89% ee). The reaction was a kinetic resolution process under mild conditions and displayed a broad substrate scope for both pyridones and allylic alcohols. The potential of this method was demonstrated by a gram-scale reaction with only 0.6 mol% catalyst loading and diverse transformations of the amination products to useful skeletons.

中文翻译：

铱催化的吡啶酮分子间不对称烯丙基胺化

我们在此报告了一种对映体富集的N-取代吡啶酮的催化合成方法。通过使用由 Carreira [P/烯烃] 配体生成的手性铱催化剂，烯丙醇与吡啶酮的分子间不对称烯丙基胺化顺利进行，具有优异的化学选择性、区域选择性和对映选择性 (>19:1 N / O , >19:1 b /l 和≥89% ee)。该反应是在温和条件下的动力学拆分过程，并且对吡啶酮和烯丙醇都显示出广泛的底物范围。这种方法的潜力通过仅 0.6 mol% 催化剂负载的克级反应和胺化产物向有用骨架的多种转化得到证明。

更新日期：2022-06-14

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