Silicon‐based Bulky Group−Tuned Parallel Kinetic Resolution in Copper‐Catalyzed 1,3‐Dipolar Additions,Advanced Synthesis & Catalysis

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Silicon‐based Bulky Group−Tuned Parallel Kinetic Resolution in Copper‐Catalyzed 1,3‐Dipolar Additions
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-04-23 , DOI: 10.1002/adsc.201800220
Yang Yuan ₁ , Zhan-Jiang Zheng ₁ , Li Li ₁ , Xing-Feng Bai _{1,

2} , Zheng Xu ₁ , Yu-Ming Cui ₁ , Jian Cao ₁ , Ke-Fang Yang ₁ , Li-Wen Xu _{1,

2}

Affiliation

The development of new strategies or reaction processes that tease new reactivity of functional groups continues to spur synthetic chemists toward innovative solutions that access new compounds. Herein, we find that the silicon‐based bulky group enables a 1,3‐dipolar addition−initiated parallel kinetic resolution (PKR) to occur unexpectedly, leading to the highly enantioselective synthesis of two structurally different types of amino acid derivatives via chemodivergent [3+2] cycloaddition reactions and tandem conjugate addition‐elimination reaction respectively. The resulting and structurally divergent enantioenriched amino acid derivatives that contain four contiguous stereogenic centers and an all‐carbon quaternary center were obtained with up to 99% ee with >95:1 dr and good yields.

中文翻译：

铜催化的1,3-偶极加成物中基于硅的大基团调节的平行动力学拆分

研发新的策略或反应过程以激发官能团的新反应性，这继续促使合成化学家们寻求使用新化合物的创新解决方案。在本文中，我们发现硅基庞大的基团使1,3-偶极加成引发的平行动力学拆分（PKR）意外发生，从而导致通过化学发散[3]产生两种结构不同类型的氨基酸衍生物的高度对映选择性[3]。 +2]分别为环加成反应和串联共轭加消除反应。得到的结果和结构上不同的对映体富集的氨基酸衍生物包含四个连续的立体生成中心和一个全碳四元中心，其ee高达99％，dr大于95：1 和高产量。

更新日期：2018-04-23

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