Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides
Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides
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DOI：
10.1002/anie.202011342
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发表时间：
2020-11-03
影响因子：
16.6
通讯作者：
Nevado, Cristina
中科院分区：
文献类型：
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作者：
Cuesta-Galisteo, Sergio;Schorgenhumer, Johannes;Nevado, Cristina
报道了镍催化的乙烯基酰胺不对称还原性氢化芳基化反应生成富集对映体的α -芳基苯酰胺。使用手性双咪唑啉（BIm）配体，结合二氧基甲基硅烷和芳基卤化物，可以在烯烃的内部位置上选择性地引入芳基，在N原子上形成一个新的立体中心。使用中性试剂和温和的反应条件，可以简单地获得抗癌、SARS-CoV PLpro抑制剂和KCNQ通道打开剂中存在的药理学相关基序。
A nickel-catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched alpha-arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center alpha to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS-CoV PLpro inhibitors, and KCNQ channel openers.