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Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin-3-amines
Cai, Xian-Feng1,2; Guo, Ran-Ning1; Chen, Mu-Wang1; Shi, Lei1; Zhou, Yong-Gui1
KeywordAromatic Amines Asymmetric Hydrogenation Chirality Exocyclic Amines
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
2014-06-10
DOI10.1002/chem.201402592
Volume20Issue:24Pages:7245-7248
Indexed BySCI ; IC ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordIRIDIUM-CATALYZED HYDROGENATION ; 2 CONTIGUOUS STEREOCENTERS ; ENANTIOSELECTIVE HYDROGENATION ; HETEROAROMATIC-COMPOUNDS ; ISOQUINOLINIUM SALTS ; FACILE ACCESS ; QUINOLINES ; QUINOXALINES ; REDUCTION ; EFFICIENT
AbstractAsymmetric 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.
Language英语
WOS IDWOS:000337617500008
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/145735
Collection中国科学院大连化学物理研究所
Affiliation1.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
Recommended Citation
GB/T 7714
Cai, Xian-Feng,Guo, Ran-Ning,Chen, Mu-Wang,et al. Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin-3-amines[J]. CHEMISTRY-A EUROPEAN JOURNAL,2014,20(24):7245-7248.
APA Cai, Xian-Feng,Guo, Ran-Ning,Chen, Mu-Wang,Shi, Lei,&Zhou, Yong-Gui.(2014).Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin-3-amines.CHEMISTRY-A EUROPEAN JOURNAL,20(24),7245-7248.
MLA Cai, Xian-Feng,et al."Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin-3-amines".CHEMISTRY-A EUROPEAN JOURNAL 20.24(2014):7245-7248.
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