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Construction of axial chirality via palladium/chiral norbornene cooperative catalysis
Nature Catalysis ( IF 37.8 ) Pub Date : 2020-08-10 , DOI: 10.1038/s41929-020-0494-1
Ze-Shui Liu , Yu Hua , Qianwen Gao , Yuanyuan Ma , Hua Tang , Yong Shang , Hong-Gang Cheng , Qianghui Zhou

Axially chiral biaryls are common structural motifs in functional materials, bioactive natural products, pharmaceuticals and chiral catalysts/ligands. As such, efficient preparation of these privileged scaffolds is an important endeavour in organic chemistry. Herein we report a general and modular platform technology for the construction of axial chirality via palladium/chiral norbornene cooperative catalysis. It is a three-component cascade process that involves widely available aryl iodides, 2,6-substituted aryl bromides and olefins (or alkynes, boronic acids and so on) as the reactants. A wide variety of substrates bearing an assortment of functional groups (88 examples) are compatible with this method. Other features include a distinct stereoinduction model, excellent enantioselectivities, step economy and scalability. This method is also amenable for the synthesis of chiral fluorenols through axial-to-central chirality transfer in high stereochemical fidelity. We anticipate that this work will have broad synthetic utilities in chiral ligands and catalyst-design for asymmetric catalysis.



中文翻译:

通过钯/手性降冰片烯协同催化构建轴向手性

轴向手性联芳基是功能材料,生物活性天然产物,药物和手性催化剂/配体中的常见结构基序。因此,这些特权支架的有效制备是有机化学中的重要努力。在这里,我们报告通过钯/手性降冰片烯协同催化构建轴向手性的通用和模块化平台技术。它是一种三组分级联过程,涉及广泛使用的芳基碘化物,2,6-取代的芳基溴化物和烯烃(或炔烃,硼酸等)作为反应物。带有多种官能团的多种底物(88个实例)与该方法兼容。其他功能包括独特的立体诱导模型,出色的对映选择性,步骤经济性和可扩展性。该方法也适用于以高立体化学保真度通过轴向中心手性转移来合成手性芴醇。我们预计这项工作将在手性配体和不对称催化的催化剂设计方面具有广泛的合成用途。

更新日期:2020-08-10
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