73789-98-7Relevant articles and documents
Access to α,α-Difluoro-γ-amino Acids by Nickel-Catalyzed Reductive Aryldifluoroacetylation of N -Vinylacetamide
Zhao, Qing-Wei,Yang, Zhi-Fang,Fu, Xia-Ping,Zhang, Xingang
supporting information, p. 1565 - 1569 (2020/11/16)
A nickel-catalyzed reductive aryldifluoroacetylation of N -vinylacetamide with ethyl chloro(difluoro)acetate and aryl iodides is described. This chelating amide carbonyl group-assisted strategy provides rapid access to a variety of protected α,α-difluoro-γ-amino acids that might have potential applications in peptide chemistry and protein engineering. An advantage of this method is its synthetic simplicity, with no preparation of organometallic reagents.
Nickel-catalyzed carbodifunctionalization of: N -vinylamides enables access to γ-amino acids
Yang, Zhi-Fang,Xu, Chang,Zheng, Xing,Zhang, Xingang
supporting information, p. 2642 - 2645 (2020/03/10)
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.
trans-Selective Aryldifluoroalkylation of Endocyclic Enecarbamates and Enamides by Nickel Catalysis
Cheng, Ran,Luo, Yun-Cheng,Wang, Ming-Kuan,Xu, Chang,Zhang, Xingang
supporting information, p. 18741 - 18747 (2020/08/26)
Efficient methods for the dicarbofuntionalization of the cyclic alkenes 2-pyrroline and 2-azetine are limited. Particularly, the dicarbofunctionalization of endocyclic enecarbamates to achieve fluorinated compounds remains an unsolved issue. Reported here is a nickel-catalyzed trans-selective dicarbofunctionalization of N-Boc-2-pyrroline and N-Boc-2-azetine, a class of endocyclic enecarbamates previously unexplored for transition metal catalyzed dicarbofunctionalization. The reaction can be extended to six- and seven-membered endocyclic enamides. A variety of arylzinc reagents and bromodifluoroacetate, and its derivatives, undergo the reaction, providing straightforward and efficient access to an array of pyrrolidine- and azetidine-containing fluorinated amino acids and oligopeptides, which may have applications in the life sciences.