An efficient route to chiral N-heterocycles bearing a C-F stereogenic center via asymmetric hydrogenation of fluorinated isoquinolines.
An efficient iridium-catalyzed asymmetric hydrogenation of the fluorinated isoquinoline derivatives has been successfully developed for the synthesis of chiral fluorinated tetrahydroisoquinoline derivatives with up to 93% ee. This methodology features the use of a hydrochloride salt as well as a catalytic amount of halogenated hydantoin which were vital for the reactivity, enantioselectivity, and inhibition of the hydrodefluorination pathway.
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China. ygzhou@dicp.ac.cn.
Ran-Ning
RN
Guo
Xian-Feng
XF
Cai
Lei
L
Shi
Zhi-Shi
ZS
Ye
Mu-Wang
MW
Chen
Yong-Gui
YG
Zhou
D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D006845:Hydrocarbons, Fluorinated; D007546:Isoquinolines; D007495:Iridium