Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin-3-amines

被引：32

作者：

Cai, Xian-Feng ^{[1
,2
]}

Guo, Ran-Ning ^{[1
]}

Chen, Mu-Wang ^{[1
]}

Shi, Lei ^{[1
]}

Zhou, Yong-Gui ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

[2] Dalian Univ Technol, Dept Chem, Dalian 116012, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 24期

基金：

中国国家自然科学基金;

关键词：

aromatic amines; asymmetric hydrogenation; chirality; exocyclic amines; IRIDIUM-CATALYZED HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; HETEROAROMATIC-COMPOUNDS; FACILE ACCESS; QUINOLINES; REDUCTION; QUINOXALINES; EFFICIENT; LIGANDS; DIFLUORPHOS;

D O I：

10.1002/chem.201402592

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 diastereo-selectivity. 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.

引用

页码：7245 / 7248

页数：4