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

页码：6273 / 6278

页数：6

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
[J]. 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
[J]. 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
[J]. 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
[J]. 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
[J]. 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
[J]. 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
[J]. 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
[J]. 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
[J]. 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
[J]. ORGANIC LETTERS, 2018, 20 (14) : 4173 - 4177

← 1 2 3 4 5 →