Preparation of Axially Chiral 2,2′-Biimidazole Ligands through Remote Chirality Delivery and Their Application in Asymmetric Carbene Insertion into N–H of Carbazoles,Organic Letters

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Preparation of Axially Chiral 2,2′-Biimidazole Ligands through Remote Chirality Delivery and Their Application in Asymmetric Carbene Insertion into N–H of Carbazoles
Organic Letters ( IF 4.9 ) Pub Date : 2019-03-28 00:00:00 , DOI: 10.1021/acs.orglett.9b00687
Hong-Qiang Shen _{1,

2} , Bo Wu ₁ , Huan-Ping Xie ₁ , Yong-Gui Zhou _{1,

3}

Affiliation

Axially chiral biimidazole ligands have been rarely synthesized and studied, in contrast to the significant achievements in the synthesis and application of central chiral imidazole ligands. Herein, a series of novel axially chiral 2,2′-biimidazole ligands were synthesized from the reaction of 2,2′-bis(bromomethyl)-1,1′-binaphthalene and 2,2′-biimidazole in one step through the strategy of remote chirality delivery. These ligands have been proven to be efficient for Cu- or Fe-catalyzed asymmetric insertion of α-aryl-α-diazoacetates into the N–H bond of carbazoles with up to 96% ee.

中文翻译：

远程手性传递法制备轴向手性2,2'-苯并咪唑配体及其在咔唑不对称碳原子插入NH中的应用

与在中心手性咪唑配体的合成和应用方面取得的显著成就相反，轴向手性联咪唑配体很少被合成和研究。在此，通过该策略一步一步地由2,2'-双（溴甲基）-1,1'-联萘与2,2'-联咪唑的反应合成了一系列新型的轴向手性2,2'-联咪唑配体手性交付。这些配体已被证明可有效地将Cu-或Fe催化的α-芳基-α-重氮乙酸酯的不对称插入ee高达96％的咔唑的N–H键中。

更新日期：2019-03-28

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