Anion effect on enantioselective oxidative NHC catalysis: highly efficient kinetic resolution of tertiary alcohols and beyond,Organic Chemistry Frontiers

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Anion effect on enantioselective oxidative NHC catalysis: highly efficient kinetic resolution of tertiary alcohols and beyond
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-11-30 , DOI: 10.1039/d2qo01506d
Dan Hu ₁ , Si Bei Poh ₂ , Feipeng Liu ₁ , Zhifeng Tu ₁ , Xia Wang ₁ , Shenci Lu ₁ , Yu Zhao ₂

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The effect of the counter-anion on enantio-control in oxidative NHC catalysis is demonstrated systematically for the first time. For kinetic resolution of oxindole-derived tertiary alcohols through NHC-catalyzed esterification, the identity of anions, either in the form of an additive or as the counter-anion in the azolium pre-catalyst, showed a significant effect on the enantioselectivity of the catalytic system. With the suitable choice of anions, highly efficient kinetic resolution (with k_rel between 30 and >200) was achieved for a wide range of oxindole-derived tertiary alcohols bearing alkyl, aryl and functionalized substituents. The anion effect on other oxidative NHC-catalyzed processes such as formal cycloaddition is also demonstrated.

中文翻译：

阴离子对对映选择性氧化 NHC 催化的影响：叔醇及其他物质的高效动力学拆分

首次系统地证明了抗衡阴离子对氧化 NHC 催化中对映体控制的影响。对于通过 NHC 催化的酯化反应对羟吲哚衍生的叔醇进行动力学拆分，阴离子的特性，无论是以添加剂的形式还是作为唑预催化剂中的抗衡阴离子，都对催化的对映选择性有显着影响系统。通过选择合适的阴离子，可以对范围广泛的带有烷基、芳基和官能化取代基的羟吲哚衍生的叔醇实现高效的动力学拆分（k _{rel在 30 和 >200 之间）。}还证明了阴离子对其他氧化 NHC 催化过程（如形式环加成）的影响。

更新日期：2022-11-30

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