Quinoxaline-specific enantioselective sulfa-michael reaction catalyzed by chiral phosphoric acid  

作　　者：Xiongfei Deng Shiqi Zhang Hesen Huang Xin Cui Zhuo Tang Guangxun Li 

机构地区：[1]Natural Products Research Center,Chengdu Institution of Biology,Chinese Academy of Sciences,Chengdu 610041,China [2]University of Chinese Academy of Sciences,Beijing 100049,China

出　　处：《Chinese Chemical Letters》2023年第12期172-176,共5页中国化学快报（英文版）

基　　金：supported by the West Light Foundation of the Chinese Academy of Sciences(No.25E0C304);the Sichuan Science and Technology Program(No.2021ZYD0061).

摘　　要：Highly enantioselective sulfa-Michael additions(SMA)between 2-alkenyl quinoxalines and aromatic thiols are accomplished using a low loading of chiral phosphoric acid catalyst(1 mol%).It was confirmed by an investigation of a lot of azaarenes that the two C-N units of quinoxalines are indispensable for controlling the reaction enantioselectivities.A series of non-terminal 2-alkenes substituted with aryls or alkyls,even other electro-withdrawing groups such as ketones,esters,or amides,selectively reacted and afforded the desired SMA products(48 examples)in good regioselectivities with high yields(up to 99%)and good ee values(up to 97%).

关 键 词：Sulfa-Michaela ddition QUINOXALINE Chiral phosphoric acid Regioselectivity ENANTIOSELECTIVITY 

分 类 号：O621.251[理学—有机化学] O626[理学—化学]