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Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin‐3‐amines
Author(s) -
Cai XianFeng,
Guo RanNing,
Chen MuWang,
Shi Lei,
Zhou YongGui
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402592
Subject(s) - enantioselective synthesis , chemistry , moiety , enantiomer , ring (chemistry) , substrate (aquarium) , organic chemistry , enantiomeric excess , asymmetric hydrogenation , combinatorial chemistry , catalysis , oceanography , geology
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.