化学
磷酸
对称化
立体中心
催化作用
手性(物理)
键裂
芳基
轴手性
电泳剂
药物化学
组合化学
有机化学
立体化学
对映选择合成
物理
量子力学
手征对称破缺
Nambu–Jona Lasinio模型
烷基
夸克
作者
Jiming Yang,Jiwei Zhang,Wen Bao,Sheng‐Qi Qiu,Shaoyu Li,Shao‐Hua Xiang,Jun Song,Junmin Zhang,Bin Tan
摘要
The previously elusive catalytic enantioselective construction of axially chiral B-aryl-1,2-azaborines with a C–B stereogenic axis has been realized through a chiral phosphoric acid-catalyzed desymmetrization strategy reported herein. The electrophilic aromatic substitution reaction of 3,5-disubsituted phenols with diazodicarboxamides could afford these axially chiral structures in good efficiency with excellent enantiocontrol. The efficient long-range stereochemical control is achieved by multiple well-defined H-bonding interactions between chiral phosphoric acid and both substrates. Meanwhile, the reaction duration could be markedly shortened with weakly acidic N–H in 1,2-azaborine acting as H-bond donor. The scalability of the reaction and facile cleavage of the N–N bond in the product further demonstrated the practicality of this method.
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