Catalytic Atroposelective Electrophilic Amination of Indoles
Jingyang Qin, Tong Zhou, Tai‐Ping Zhou, Langyu Tang, Honghua Zuo, Huaibin Yu, Guojiao Wu, Yuzhou Wu, Rong‐Zhen Liao, Fangrui Zhong
Abstract
Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N-sulfonyl-3-arylaminoindoles with excellent optical purity. This reaction was furnished by 1,6-nucleophilic addition to p-quinone diimines. Control experiments suggest an ionic mechanism that differs from the radical addition pathway commonly proposed for 1,6-addition to quinones. The origin of 1,6-addition selectivity was investigated through computational studies. Preliminary studies show that the obtained 3-aminoindoles atropisomers exhibit anticancer activities. This method is valuable with respect to enlarging the toolbox for atropochiral amine derivatives.