Organic Photoredox-Catalyzed Site-Selective Alkylation of Glycine Derivatives and Peptides via Infrequent 1,2-Hydrogen Atom Transfer of Amidyl Radicals

被引：4
|
作者：
Hou, Jinyu [1 ,2 ,3 ]
Fan, Hongying [1 ,2 ,3 ]
Zhang, Xue [1 ,2 ,3 ]
Liu, Xingyu [1 ,2 ,3 ]
Chen, Jian [1 ,2 ,3 ]
Lv, Guanghui [4 ]
He, Shiyun [1 ,2 ,3 ]
Hai, Li [1 ,2 ,3 ]
Yang, Zhongzhen [5 ]
Wu, Yong [1 ,2 ,3 ]
机构：
[1] Sichuan Univ, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Chengdu 610041, Sichuan, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Sichuan Engn Lab Plant Sourced Drug, Chengdu 610041, Sichuan, Peoples R China
[3] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China
[4] Hubei Univ Med, Taihe Hosp, Hubei Key Lab Embryon Stem Cell Res, Shiyan 442000, Hubei, Peoples R China
[5] Sichuan Univ, West China Hosp, Dept Pharm, Chengdu 610041, Peoples R China
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 36期
关键词：
ALPHA; BETA-DIAMINO ACIDS; BIOLOGICAL SIGNIFICANCE; BOND FORMATION;
D O I：
10.1021/acs.orglett.4c02742
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we disclose a visible-light-driven photoredox-catalyzed protocol for site-selective alkylation of glycine derivatives via 1,2-hydrogen atom transfer, which is distinguished by metal free and mild conditions, high chemoselectivity, and good functional group compatibility. This protocol provides a unique approach for synthesizing valuable alpha,beta-diamino acid derivatives. Furthermore, the potential synthetic merit of this transformation is proven by a scale-up reaction and late-stage functionalization of peptides.
引用
收藏
页码：7638 / 7643
页数：6
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