Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C_(6)F_(5))_(3)/chiral phosphoric acid  

作　　者：Zhen Liu Zhi-Yuan Ren Chen Yang Xiangyi Shao Li Chen Xin Li 

机构地区：[1]State Key Laboratory of Elemento-Organic Chemistry,Frontiers Science Center for New Organic Matter,College of Chemistry,Nankai University,Tianjin 300071,China [2]Haihe Laboratory of Sustainable Chemical Transformations,Tianjin 300192,China [3]Zhenhai High School of Zhejiang,Ningbo 315299,China

出　　处：《Chinese Chemical Letters》2024年第5期135-140,共6页中国化学快报（英文版）

基　　金：National Natural Science Foundation of China(Nos.22193011,21971120 and 21933008);National Science&Technology Fundamental Resource Investigation Program of China(No.2018FY201200)for financial support.

摘　　要：Catalytic enantioselective alkenylation is an efficient method to construct chiral alkene molecules,but the asymmetric alkenylation of simple alkenes catalyzed by metal-free catalysts remains an elusive challenge.Herein,we reported an asymmetric alkenylation of benzoxazinones with diarylethylenes by utilizing a B(C_(6)F_(5))_(3)/chiral phosphoric acid catalyst.A broad of benzoxazinones and diarylethylenes with electron-withdrawing and electron-donating groups were tolerated(up to 95%yield and 97.5:2.5 e.r.)in the methodology under mild reaction conditions.Moreover,the synthetic utility was confirmed by the scaled-up reaction and transformations of the products.The mechanism was preliminarily explored by control reactions,nonlinear effect experiment and DFT calculations.

关 键 词：Asymmetric alkenylation Simple alkenes BENZOXAZINONES B(C_(6)F_(5))_(3)/chiral phosphoric acid Theoretical calculations 

分 类 号：O621.251[理学—有机化学]