Synthesis of chiral exocyclic amines by asymmetric hydrogenation of aromatic quinolin-3-amines.
Asymmetric hydrogenation of aromatic quinolin-3-amines was successfully developed with up to 94 % enantiomeric excess (ee). Introduction of the phthaloyl moiety to the amino group is crucial to eliminate the inhibition effect caused by the substrate and product, to activate the aromatic ring, and to improve the diastereoselectivity. This new methodology provides direct and facile access to chiral exocyclic amines. Notably, this report is the first on the highly enantioselective hydrogenation of aromatic amines.
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P. R. China), Fax: (+86) 411-84379220; Department of Chemistry, Dalian University of Technology, Dalian 116012 (P. R. China).
Xian-Feng
XF
Cai
Ran-Ning
RN
Guo
Mu-Wang
MW
Chen
Lei
L
Shi
Yong-Gui
YG
Zhou
aromatic amines; asymmetric hydrogenation; chirality; exocyclic amines