Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Institute of Pharmacy and Pharmacology, University of South China, Hengyang, Hunan 421001, China.
Chem Commun (Camb). 2020 Feb 28;56(17):2642-2645. doi: 10.1039/c9cc09866f. Epub 2020 Feb 5.
A nickel-catalyzed tandem reaction of N-vinylamides with arylboronic acids and bromodifluoroacetate has been developed. The use of amide carbonyl as a chelating group efficiently furnishes a series of protected α,α-difluoro-γ-amino acid esters. The reaction can also extend to bromoacetate and 2-bromomalonate. The advantages of this protocol are high functional group tolerance and a broad substrate scope, including a variety of N-vinylamides. In particular, the use of removable amide carbonyl groups provides potential opportunities for applications in peptide chemistry and protein engineering.
镍催化的 N-乙烯酰胺与芳基硼酸和溴二氟乙酸酯的串联反应已经被开发出来。酰胺羰基作为螯合基团的使用有效地提供了一系列保护的α,α-二氟-γ-氨基酸酯。该反应也可以扩展到溴乙酸酯和 2-溴丙二酸酯。该方法的优点是具有高的官能团容忍度和广泛的底物范围，包括各种 N-乙烯酰胺。特别是，使用可去除的酰胺羰基基团为在肽化学和蛋白质工程中的应用提供了潜在的机会。
