Highly Enantioselective Synthesis of Indolines: Asymmetric Hydrogenation at Ambient Temperature and Pressure with Cationic Ruthenium Diamine Catalysts.
A highly enantioselective synthesis of indolines by asymmetric hydrogenation of 1H-indoles and 3H-indoles at ambient temperature and pressure, catalyzed by chiral phosphine-free cationic ruthenium complexes, has been developed. Excellent enantio- and diastereoselectivities (up to >99 % ee, >20:1 d.r.) were obtained for a wide range of indole derivatives, including unprotected 2-substituted and 2,3-disubstituted 1H-indoles, as well as 2-alkyl- and 2-aryl-substituted 3H-indoles.
CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China.|College of Chemistry, Xiangtan University, Xiangtan, Hunan, 411105, P.R. China.
Zhusheng
Z
Yang
CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China. chenfei211@iccas.ac.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China. chenfei211@iccas.ac.cn.
Fei
F
Chen
CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China.
Yanmei
Y
He
College of Chemistry, Xiangtan University, Xiangtan, Hunan, 411105, P.R. China.
Nianfa
N
Yang
CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China. fanqh@iccas.ac.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China. fanqh@iccas.ac.cn.
Qing-Hua
QH
Fan
N ligands; heterocycles; hydrogenation; indoles; ruthenium