Synthesis of chiral piperazin-2-ones through palladium-catalyzed asymmetric hydrogenation of pyrazin-2-ols

被引:9
作者
Feng, Guang-Shou [1 ]
Zhao, Zi-Biao [1 ]
Shi, Lei [2 ]
Zhou, Yong-Gui [1 ,3 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
[2] Dalian Univ Technol, Sch Chem Engn, Dalian 116024, Peoples R China
[3] Dalian Univ Technol, Zhang Dayu Sch Chem, Dalian 116024, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 22期
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; PIPERAZINONE RINGS; TETRAHYDROPYRAZINES; PSEUDOTHEONAMIDES; 2-OXOPIPERAZINES; PYRAZINES;
D O I
10.1039/d1qo01144h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed asymmetric hydrogenation of pyrazines containing a tautomeric hydroxyl group has been developed, providing a facile access to chiral disubstituted piperazin-2-ones with excellent diastereoselectivities and enantioselectivities. The product could be conveniently converted into chiral piperazines without loss of optical purity.
引用
收藏
页码:6273 / 6278
页数:6
相关论文
共 50 条
  • [41] Ligand-Controlled, Palladium-Catalyzed Asymmetric [4+4] and [2+4] Cycloadditions
    Li, Qiuyu
    Pan, Rui
    Wang, Meihui
    Yao, Hequan
    Lin, Aijun
    ORGANIC LETTERS, 2021, 23 (06) : 2292 - 2297
  • [42] Inverse-Electron-Demand Palladium-Catalyzed Asymmetric [4+2] Cycloadditions Enabled by Chiral P,S-Ligand and Hydrogen Bonding
    Wang, Ya-Ni
    Xiong, Qin
    Lu, Liang-Qiu
    Zhang, Qun-Liang
    Wang, Ying
    Lan, Yu
    Xiao, Wen-Jing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) : 11013 - 11017
  • [43] Rh-Catalyzed Asymmetric Hydrogenation of 2-Substituted 4H-(Thio)chromenes for Synthesis of Chiral (Thio)chromanes
    Wu, Xiaoxue
    Li, Meina
    Guo, Qianling
    Zi, Guofu
    Hou, Guohua
    ORGANIC LETTERS, 2024, 26 (28) : 5917 - 5922
  • [44] Design and Synthesis of Planar-Chiral Oxazole-Pyridine N,N-Ligands: Application in Palladium-Catalyzed Asymmetric Acetoxylative Cyclization
    Bai, Yu-Qing
    Wang, Xin-Wei
    Wu, Bo
    Wang, Xiao-Qing
    Liao, Rong-Zheng
    Li, Man
    Zhou, Yong-Gui
    ACS CATALYSIS, 2023, 13 (14) : 9829 - 9838
  • [45] Highly Enantioselective Synthesis of Planar-Chiral Cyclophanes through a Brønsted Acid-Catalyzed Asymmetric Transfer Hydrogenation
    Li, Jiayan
    Zhao, Changgui
    ACS CATALYSIS, 2023, 13 (21) : 14155 - 14162
  • [46] Palladium-catalyzed synthesis of 2-amino ketones from propargylic carbonates and secondary amines
    Cacchi, Sandro
    Fabrizi, Giancarlo
    Filisti, Eleonora
    Goggiamani, Antonella
    Iazzetti, Antonia
    Maurone, Loredana
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (24) : 4699 - 4703
  • [47] Palladium-Catalyzed Asymmetric Tandem [3+2] Cycloaddition/Allylation Reaction of Methylene-Trimethylenemethane: Access to Chiral Tricyclic Dinitrogen-Fused Heterocycles
    Mao, Biming
    Xu, Yi
    Chen, Yuehua
    Dong, Jipan
    Zhang, Junya
    Gu, Kejia
    Zheng, Bing
    Guo, Hongchao
    ORGANIC LETTERS, 2019, 21 (12) : 4424 - 4427
  • [48] Kinetic Resolution of 2-Substituted 2,3-Dihydro-4-pyridones by Palladium-Catalyzed Asymmetric Allylic Alkylation: Catalytic Asymmetric Total Synthesis of Indolizidine (-)-209I
    Lei, Bai-Lin
    Zhang, Qing-Song
    Yu, Wei-Hua
    Ding, Qiu-Ping
    Ding, Chang-Hua
    Hou, Xue-Long
    ORGANIC LETTERS, 2014, 16 (07) : 1944 - 1947
  • [49] Synthesis of Multisubstituted 2,3-Allenamides via Palladium-Catalyzed Carbonylation of Propargylic Esters
    Zhang, Zhi
    Ji, Miao-Miao
    Wu, Xiao-Feng
    He, Yong-Yu
    Peng, Jin-Bao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12) : 9001 - 9010
  • [50] Enantioselective Access to Chiral 2-Substituted 2,3-Dihydrobenzo[1,4]dioxane Derivatives through Rh-Catalyzed Asymmetric Hydrogenation
    Yin, Xuguang
    Huang, Yi
    Chen, Ziyi
    Hu, Yang
    Tao, Lin
    Zhao, Qingyang
    Dong, Xiu-Qin
    Zhang, Xumu
    ORGANIC LETTERS, 2018, 20 (14) : 4173 - 4177