Single step synthesis of β- and γ- aryl-substituted ß- and γ-amino acid derivatives by electrochemistry

被引:3
作者
Pavlovic, Barbara [1 ]
Heubel, Christoph [1 ]
Kurz, Michael [1 ]
Oehl, Elisabeth [1 ]
Waldvogel, Siegfried R. [2 ]
Mendez, Maria [1 ]
Ruf, Sven [1 ]
机构
[1] Sanofi R&D Integrated Drug Discovery, Industriepark Hochst, D-65926 Frankfurt, Germany
[2] Johannes Gutenberg Univ Mainz, Dept Chem, D-55128 Mainz, Germany
关键词
Electrochemistry; DCC coupling; Trifunctional building blocks; ss -amino acid; gamma-aminoacid; Nickel catalyzed; PEPTIDES; ESTERS;
D O I
10.1016/j.bmcl.2024.129614
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Electrochemical transformations are a subject of increasing interest in early drug discovery due to its ability to assemble complex scaffolds under rather mild reaction conditions. In this context, we became interested in electrochemical decarboxylative cross-coupling (DCC) protocols of redox-active esters (RAEs) and halo(hetero) arenes. Starting with the one-step electrochemical synthesis of novel methylamino-substituted heterocycles we recognized the potential of this methodology to deliver a novel approach to beta- and gamma- amino acids by starting from the corresponding RAEs. Our work finally resulted in the delivery of novel and highly valuable trifunctional building blocks based on ss- and gamma-amino-acid scaffolds.
引用
收藏
页数:5
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