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Direct Construction of NOBINs via Domino Arylation and Sigmatropic Rearrangement Reactions
Chinese Journal of Chemistry ( IF 5.4 ) Pub Date : 2020-07-13 , DOI: 10.1002/cjoc.202000358
Ji‐Wei Zhang 1, 2 , Liang‐Wen Qi 2 , Shaoyu Li 2, 3 , Shao‐Hua Xiang 2, 3 , Bin Tan 2
Affiliation  

Privileged 2‐amino‐2’‐hydroxy‐1,1’‐binaphthyl (NOBIN) frameworks were constructed through a novel domino arylation of naphthylhydroxylamines with diarylhalonium salts and sigmatropic rearrangement in a transition metal‐free fashion. This protocol bears broad substrate generality and proceeds under mild reaction conditions, affording diversified NOBINs in high efficiency with absolute regiocontrol during the rearrangement process. Optically active product was accessible by chiral N‐heterocyclic carbene‐catalyzed kinetic resolution in one pot or diastereoselective [3,3]‐rearrangement guided by a removable chiral auxiliary. Remarkably, diarylchloronium and diarylbrominium salts have been employed as arylation reagents for the first time in assembling such representative biaryl frameworks.

中文翻译:

通过多米诺骨化和适体重排反应直接构建NOBIN

通过萘基羟胺与二芳基hal盐的新型多米诺芳基化和无过渡金属的σ重排,构建了优先的2-氨基-2'-羟基-1,1'-联萘(NOBIN)骨架。该方案具有广泛的底物通用性,可在温和的反应条件下进行,可在重排过程中以绝对的区域控制高效提供多样化的NOBIN。旋光性产物可通过一锅中手性N杂环卡宾催化的动力学拆分或由可移动手性助剂引导的非对映选择性[3,3]重排获得。值得注意的是,在组装这种代表性的联芳基骨架时,二芳基氯鎓盐和二芳基溴化salts盐首次被用作芳基化试剂。
更新日期:2020-07-13
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