Visible-Light-Driven Three-Component Reaction of Unactivated Alkenes Enables Access to Monofluoro ?-Amino Acids

被引：0

作者：

Ju, Guodong ^{[1
]}

Huang, Zhibin ^{[1
]}

Liu, Jian ^{[1
]}

Xu, Xu ^{[1
]}

Deng, Zefeng ^{[1
]}

Zhao, Yingsheng ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453000, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年

关键词：

visible-light-driven; three-component reaction; quinoxalinones; monofluoro & gamma; -amino acids; unactivated alkenes;

D O I：

10.1002/ejoc.202300596

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy for the synthesis of diverse protected a-monofluoro-?-amino acid derivatives has been developed. This reaction assembles a simple enamide, quinoxalin-2(1H)-one, and diethyl 2-bromo-2-fluoromalonate through a three-component reaction driven by visible light. The advantages of this protocol include the simplicity of its operation, mild conditions, high functional group tolerance, and applicability to a wide variety of substrates. The synthesis of this fluorine-containing amino acid derivative has significant value for potential applications in medicinal chemistry and chemical biology.

引用

页数：6

共 50 条

[41] Photocatalyst-free visible-light-mediated three-component reaction ofα-diazoesters, cyclic ethers and NaSCN to access organic thiocyanates
Zhiwei Wang
Na Meng
Yufen Lv
Wei Wei
Huilan Yue
Guofu Zhong
Chinese Chemical Letters, 2023, 34 (02) : 230 - 233
[42] Visible light-mediated three-component functionalization of olefins with sulfoxyimidoylsulfonium salt for the synthesis of β-amino alcohols and amino ethers
Xie, Wei
Zhao, Liang
Fu, Xinmei
Zhang, Rong
Hao, Xinyu
Duan, Chunying
Li, Yaming
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (23) : 4909 - 4912
[43] General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis
Guo, Lei
Yuan, Mingbin
Zhang, Yanyan
Wang, Fang
Zhu, Shengqing
Gutierrez, Osvaldo
Chu, Lingling
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (48) : 20390 - 20399
[44] Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines
Yang, Sen
Qiu, Chao-Ying
Hu, Hao
Jiang, Yan
Chen, Ming
ORGANIC LETTERS, 2024, 26 (39) : 8416 - 8423
[45] General Method for Selective Three-Component Carboacylation of Alkenes via Visible-Light Dual Photoredox/Nickel Catalysis
Wang, Zi-Kai
Wang, Ya-Ping
Rao, Zhi-Wu
Liu, Chun-Yu
Pan, Xian-Hua
Guo, Lei
ORGANIC LETTERS, 2023, 25 (10) : 1673 - 1677
[46] Ni-catalyzed enantioselective three-component reductive alkylacylation of alkenes: modular access to structurally complex α-amino ketones
Xiao, Jichao
Jia, Tingting
Chen, Shuang
Pan, Mengxiao
Li, Xingwei
CHEMICAL SCIENCE, 2024, 15 (37) : 15489 - 15495
[47] Highly selective three-component coupling of ethyl propiolate, alkenes, and diphenyl diselenide under visible-light irradiation
Ogawa, A
Doi, M
Ogawa, I
Hirao, T
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (13-14) : 2027 - 2029
[48] Visible-Light-Mediated Trifluoroalkylation of Isoquinolines via Three-Component Minisci-Type Reaction
Thakur, Ankita
Gupta, Shiv Shankar
Sharma, Upendra
ORGANIC LETTERS, 2024, 26 (40) : 8515 - 8520
[49] Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction
Lipp, Benjamin
Kammer, Lisa Marie
Kuecuekdisli, Murat
Luque, Adriana
Kuehlborn, Jonas
Pusch, Stefan
Matuleviciute, Gita
Schollmeyer, Dieter
Sackus, Algirdas
Opatz, Till
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (38) : 8965 - 8969
[50] Molecular diversity of the three-component reaction of α-amino acids, dialkyl acetylenedicarboxylates and N-substituted maleimides
Chen, Liang
Sun, Jing
Xie, Ju
Yan, Chao-Guo
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (27) : 6497 - 6507

← 1 2 3 4 5 →