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 |
DOI | 10.1021/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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