Efficient Synthesis of Biaryl-Bridged Seven-Membered Lactones via N-Heterocyclic Carbene Catalyzed Dynamic Kinetic Resolution
Huan Gong , Hongzhi Zhuang , Yang Xiao , Yao Chen , Xiaoqing Lai , Zhuofeng Deng , Jianing An , Yiqun Li , Jianfeng Xu , Xingkuan Chen
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (18) : 2318 -2324.
Efficient Synthesis of Biaryl-Bridged Seven-Membered Lactones via N-Heterocyclic Carbene Catalyzed Dynamic Kinetic Resolution
Bridged biaryl atropisomers are widely recognized as a significant structural motif commonly found in bioactive molecules and natural products. Herein, we report an organocatalytic dynamic kinetic resolution (DKR) approach for the synthesis of optically pure biaryl-bridged seven-membered lactones. In the presence of a chiral N-heterocyclic carbene (NHC) catalyst, racemic biaryl-bridged hemiacetals, generated in situ from 2’-formyl-2-biphenyl carboxylic acids, undergo stereoselective coupling with NHC-bound acylazolium intermediates derived from NHC and aldehydes. This transformation delivers seven-membered biaryl-bridged lactone products with very high yields and good to excellent regio- and enantioselectivities.
Asymmetric catalysis / Biary-bridged molecules / Dynamic kinetic resolution / N-Heterocyclic carbenes / Seven-membered ring
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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