Copper-catalyzed desymmetric intramolecular Ullmann C-N coupling: an enantioselective preparation of indolines.
The first highly enantioselective copper-catalyzed intramolecular Ullmann C-N coupling reaction has been developed. The asymmetric desymmetrization of 1,3-bis(2-iodoaryl)propan-2-amines catalyzed by CuI/(R)-BINOL-derived ligands led to the enantioselective formation of indolines in high yields and excellent enantiomeric excesses. This method was also applied to the formation of 1,2,3,4-tetrahydroquinolines in high yields and excellent enantioselectivity.
Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, China.
Fengtao
F
Zhou
Jiajia
J
Guo
Jianguang
J
Liu
Ke
K
Ding
Shouyun
S
Yu
Qian
Q
Cai
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007211:Indoles; C057812:indoline; D002244:Carbon; D003300:Copper; D009584:Nitrogen