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Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers
Feng, Guang-Shou1,2; Chen, Mu-Wang1; Shi, Lei1; Zhou, Yong-Gui1
KeywordCyclic Ureas Palladium Pyrimidines Tautomerization 1 3-diamines
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2018-05-14
ISSN1433-7851
DOI10.1002/anie.201801485
Volume57Issue:20Pages:5853-5857
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordCATALYZED ASYMMETRIC HYDROGENATION ; MULTIPLE STEREOGENIC CENTERS ; ENANTIOSELECTIVE SYNTHESIS ; PYRIDINIUM SALTS ; HETEROAROMATIC-COMPOUNDS ; BIGINELLI REACTION ; DERIVATIVES ; IMINES ; ACID ; 1,3-DIAMINES
AbstractA facile access to optically active cyclic ureas was developed through palladium-catalyzed asymmetric hydrogenation of pyrimidines containing tautomeric hydroxy group with up to 99% ee. Mechanistic studies indicated that reaction pathway proceed through hydrogenation of C=N of the oxo tautomer pyrimidin-2(1H)-one, acid-catalyzed isomerization of enamine-imine, and hydrogenation of imine pathway. In addition, the chiral cyclic ureas are readily converted into useful chiral 1,3-diamine and thiourea derivatives without loss of optical purity.
Language英语
WOS IDWOS:000431488200049
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Cited Times:11[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/167149
Collection中国科学院大连化学物理研究所
Corresponding AuthorShi, Lei; Zhou, Yong-Gui
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Feng, Guang-Shou,Chen, Mu-Wang,Shi, Lei,et al. Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2018,57(20):5853-5857.
APA Feng, Guang-Shou,Chen, Mu-Wang,Shi, Lei,&Zhou, Yong-Gui.(2018).Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,57(20),5853-5857.
MLA Feng, Guang-Shou,et al."Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57.20(2018):5853-5857.
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