Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers

doi:10.1002/anie.201801485

	Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers
	Shi, Lei 1; Feng, Guang-Shou 1,2; Chen, Mu-Wang 1; Zhou, Yong-Gui 1
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2018-05-14
卷号	57 期号:20 页码:5853-5857
关键词	Cyclic Ureas Palladium Pyrimidines Tautomerization 1 3-diamines
ISSN号	1433-7851
DOI	10.1002/anie.201801485
文献子类	Article
英文摘要	A 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.
WOS关键词	CATALYZED ASYMMETRIC HYDROGENATION ; MULTIPLE STEREOGENIC CENTERS ; ENANTIOSELECTIVE SYNTHESIS ; PYRIDINIUM SALTS ; HETEROAROMATIC-COMPOUNDS ; BIGINELLI REACTION ; DERIVATIVES ; IMINES ; ACID ; 1,3-DIAMINES
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000431488200049
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/167148]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Shi, Lei; Zhou, Yong-Gui
作者单位	1.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
推荐引用方式 GB/T 7714	Shi, Lei,Feng, Guang-Shou,Chen, Mu-Wang,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	Shi, Lei,Feng, Guang-Shou,Chen, Mu-Wang,&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	Shi, Lei,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.