Iridium-Catalyzed Asymmetric Hydrogenation of 4,6-Disubstituted 2-Hydroxypyrimidines
Chen, Mu-Wang1; Feng, Guang-Shou1; Shi, Lei1; Meng, Fan-Jie1; Zhou, Yong-Gui1,2
刊名ORGANIC LETTERS
2018-10-19
卷号20期号:20页码:6415-6419
ISSN号1523-7060
DOI10.1021/acs.orglett.8b02723
通讯作者Shi, Lei(shileichem@dicp.ac.cn) ; Zhou, Yong-Gui(ygzhou@dicp.ac.cn)
英文摘要An efficient iridium-catalyzed hydrogenation of 4,6-disubstituted 2-hydroxypyrimidines has been achieved, giving chiral cyclic ureas with excellent diastereoselectivities and up to 96% ee of enantioselectivities. In the presence of the in situ generated hydrogen halide, the equilibrium of the lactame-lactime tautomerism of 2-hydroxypyrimidine is more toward the oxo form with lower aromaticity, which effectively improves the reactivity to facilitate hydrogenation. Moreover, the cyclic ureas could be readily converted into chiral 1,3-diamine derivatives without loss of optical purity.
资助项目National Natural Science Foundation of China[21772195] ; National Natural Science Foundation of China[21532006] ; Chinese Academy of Sciences[QYZDJ-SSW-SLH035] ; Dalian Bureau of Science and Technology[2016RD07]
WOS关键词HIGHLY ENANTIOSELECTIVE HYDROGENATION ; MULTIPLE STEREOGENIC CENTERS ; HETEROAROMATIC-COMPOUNDS ; ISOQUINOLINIUM SALTS ; PYRIDINIUM SALTS ; EFFICIENT ROUTE ; IONIC LIQUID ; QUINOLINES ; QUINOXALINES ; INDOLES
WOS研究方向Chemistry
语种英语
出版者AMER CHEMICAL SOC
WOS记录号WOS:000448488200022
资助机构National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese Academy of Sciences ; Chinese Academy of Sciences ; Dalian Bureau of Science and Technology ; Dalian Bureau of Science and Technology ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese Academy of Sciences ; Chinese Academy of Sciences ; Dalian Bureau of Science and Technology ; Dalian Bureau of Science and Technology ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese Academy of Sciences ; Chinese Academy of Sciences ; Dalian Bureau of Science and Technology ; Dalian Bureau of Science and Technology ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese Academy of Sciences ; Chinese Academy of Sciences ; Dalian Bureau of Science and Technology ; Dalian Bureau of Science and Technology
内容类型期刊论文
源URL[http://cas-ir.dicp.ac.cn/handle/321008/166750]  
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.Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
推荐引用方式
GB/T 7714
Chen, Mu-Wang,Feng, Guang-Shou,Shi, Lei,et al. Iridium-Catalyzed Asymmetric Hydrogenation of 4,6-Disubstituted 2-Hydroxypyrimidines[J]. ORGANIC LETTERS,2018,20(20):6415-6419.
APA Chen, Mu-Wang,Feng, Guang-Shou,Shi, Lei,Meng, Fan-Jie,&Zhou, Yong-Gui.(2018).Iridium-Catalyzed Asymmetric Hydrogenation of 4,6-Disubstituted 2-Hydroxypyrimidines.ORGANIC LETTERS,20(20),6415-6419.
MLA Chen, Mu-Wang,et al."Iridium-Catalyzed Asymmetric Hydrogenation of 4,6-Disubstituted 2-Hydroxypyrimidines".ORGANIC LETTERS 20.20(2018):6415-6419.
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