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RuPHOX‐Ru Catalyzed Asymmetric Cascade Hydrogenation of 3‐Substituted Chromones for the Synthesis of Corresponding Chiral Chromanols​
Chemistry - A European Journal ( IF 4.3 ) Pub Date : 2024-05-02 , DOI: 10.1002/chem.202400978
Shaofeng Xu 1 , Wenqi Xu 1 , Siqi Dong 1 , Delong Liu 1 , Wanbin Zhang 2
Affiliation  

An efficient RuPHOX‐Ru catalyzed asymmetric cascade hydrogenation of 3‐substituted chromones has been achieved under mild reaction conditions, affording the corresponding chiral 3‐substituted chromanols in high yields with excellent enantio‐ and diastereoselectivities (up to 99% yield, >99% ee and >20:1 dr). Control reactions and deuterium labelling experiments revealed that a dynamic kinetic resolution process occurs during the subsequent hydrogenation of the C=O double bond, which is responsible for the high performance of the asymmetric cascade hydrogenation. The resulting products allow for several transformations and it was shown that the protocol provides a practical and alternative strategy for the synthesis of chiral 3‐substituted chromanols and their derivatives.

中文翻译:

RuPHOX-Ru 催化 3-取代色酮的不对称级联氢化反应合成相应的手性色醇

在温和的反应条件下实现了高效的 RuPHOX-Ru 催化 3-取代色酮的不对称级联氢化,以高产率提供相应的手性 3-取代色酮,并具有优异的对映和非对映选择性(高达 99% 产率,>99% ee)和 >20:1 dr)。对照反应和氘标记实验表明,在随后的C=O双键氢化过程中发生了动态动力学拆分过程,这是不对称级联氢化的高性能的原因。所得产物允许进行多次转化,并且表明该方案为手性 3 取代苯并二氢吡喃醇及其衍生物的合成提供了实用且替代的策略。
更新日期:2024-05-02
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