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Olefin functionalization/isomerization enables stereoselective alkene synthesis
Nature Catalysis ( IF 37.8 ) Pub Date : 2021-07-29 , DOI: 10.1038/s41929-021-00658-2
Chen-Fei Liu 1 , Hongyu Wang 1 , Robert T Martin 2 , Haonan Zhao 1 , Osvaldo Gutierrez 2 , Ming Joo Koh 1
Affiliation  

Despite tremendous efforts aimed at devising methods for stereoselective alkene synthesis, critical challenges are yet to be addressed. Direct access to a diverse range of 1-aryl(boryl)-1-methyl-functionalized tri- and tetrasubstituted trans alkenes, entities that are prevalent in many important molecules, through a catalytic manifold from readily available α-olefin substrates remains elusive. Here, we demonstrate that catalytic amounts of a non-precious N-heterocyclic carbene–Ni(I) complex in conjunction with a sterically bulky base promote site- and trans-selective union of monosubstituted olefins with a wide array of electrophilic reagents to deliver tri- and tetrasubstituted alkenes in up to 92% yield and >98% regio- and stereoselectivity. The protocol is amenable to the preparation of carbon- and heteroatom-substituted C=C bonds, providing distinct advantages over existing transformations. Utility is highlighted through concise stereoselective synthesis of biologically active compounds.



中文翻译:

烯烃官能化/异构化使立体选择性烯烃合成成为可能

尽管在设计立体选择性烯烃合成方法方面付出了巨大努力,但仍有待解决的关键挑战。通过来自现成的 α-烯烃底物的催化歧管直接获得各种 1-芳基(硼基)-1-甲基官能化的三和四取代的反式烯烃(在许多重要分子中普遍存在的实体)仍然难以捉摸。在这里,我们证明催化量的非贵重N-杂环卡宾-Ni(I) 配合物与空间庞大的碱基结合促进位点和反式单取代烯烃与多种亲电子试剂的选择性结合,以高达 92% 的产率和 >98% 的区域和立体选择性提供三取代和四取代烯烃。该协议适用于制备碳和杂原子取代的 C=C 键,与现有的转换相比具有明显的优势。通过生物活性化合物的简洁立体选择性合成突出了实用性。

更新日期:2021-07-29
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