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Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids

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Abstract

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.

Graphical abstract: Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids

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Article information


Submitted
20 Dec 2019
Accepted
28 Jan 2020
First published
28 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids

Z. Yang, C. Xu, X. Zheng and X. Zhang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09866F

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