Carbene-Catalyzed Asymmetric Ring-Opening Reaction of Biaryl Lactams to Access Axially Chiral Biaryls  

作　　者：Guanjie Wang Guowei Yuan Chenlong Wei Ye Zhang Haibin Zhu Weiqi Yang Dongping Shi Xiaoxiang Zhang Zhenqian Fu 

机构地区：[1]Institute of Advanced Materials,Nanjing Tech University,Nanjing,Jiangsu 211816,China [2]Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources,College of Chemical Engineering,Nanjing Forestry University,Nanjing,Jiangsu 210037,China

出　　处：《Chinese Journal of Chemistry》2024年第15期1734-1740,共7页中国化学（英文版）

基　　金：the Natural Science Foundation of Jiangsu Province(BK20221309);the National Natural Science Foundation of China(21602105).

摘　　要：Axially chiral biaryls represent the most important class of atropisomers,and they widely exist in natural products and biologically active molecules.They also constitute a unique scaffold for chiral ligands and catalysts in organic synthesis.The development of synthetic methods to obtain such chiral compounds has received widespread attention,among which catalytically atroposelective ring-opening of configurationally labile compounds represents one of the most attractive strategies.Various substrates with strained cyclic structures,such as the renowned Bringmann's lactones,can undergo asymmetric transformation into stable atropisomers.Known advancement primarily relies on metal catalyst combined with well-designed chiral ligands,the approaches utilizing organocatalysis as a critical resolution strategy are notably scarce.In this study,we disclosed a N-heterocyclic carbene(NHC)-catalyzed asymmetric ring-opening reaction of biaryl lactams via direct atroposelective nucleophilic activation.The optimized bulky carbene catalyst ensures that the reaction can proceed under mild conditions,affording the desired product with good to excellent yields and atroposelectivity.

关 键 词：N-Heterocyclic carbene Axially chiral biaryls Organocatalysis Ring-opening reactions Dibenzo cyclic lactams Axially chiral amino acids Amide C-N bond activation ATROPISOMERISM Asymmetric catalysis LACTAMS 

分 类 号：O62[理学—有机化学]