摘要
以喹啉醛与芳胺化合物的不对称还原胺化为关键步骤,设计合成了一类C_(1)-对称且兼具手性并环与大位阻N-取代基两种优势结构单元的手性氮杂环卡宾配体.进一步以钯催化的分子内α-芳基化反应和铜催化的功能化烯烃质子硼化反应为模型反应,详细研究了该类配体的结构与催化性能的关系,发现四氢喹啉骨架上的8-位取代基以及大位阻手性N-取代基均对提升配体的手性诱导能力具有重要作用.
A class of C_(1)-symmetric chiral N-heterocyclic carbene(NHC)ligands,incorporating both chiral fused-ring and sterically hindered N-substituted groups,were designed and synthesized,with the asymmetric reductive amination of quinoline aldehyde with arylamine compounds as the key step.Subsequently,using palladium-catalyzed intramolecular α-arylation and copper-catalyzed protoboration of functionalization of alkenes as the model reactions,the relationship between the structure of these ligands and their catalytic performance was systematically investigated.It was found that the 8-substituted groups on the tetrahydroquinoline scaffold and the bulky chiral N-substituted groups played important roles in enhancing the chiral induction ability of the ligands.
作者
孟庆端
韩佳宏
潘一骁
郝伟
范青华
Meng Qingduan;Han Jiahong;PanYixiao;Hao Wei;Fan Qing-Hua(Beijing National Laboratory for Molecular Sciences,CAS Key Laboratory of Molecular Recognition and Function,Institute of Chemistry,Chinese Academy of Sciences,Beijing 100190;University of Chinese Academy of Sciences,Beijing 100049)
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
2023年第10期1271-1279,共9页
Acta Chimica Sinica
基金
国家重点研发计划(No.2021YFA1500200)
国家自然科学基金(Nos.92056108,92256303)资助.
关键词
手性氮杂环卡宾配体
不对称催化
钯催化
铜催化
还原胺化
chiral N-heterocyclic carbene ligand
asymmetric catalysis
Pd catalysis
Cu catalysis
reductive amination