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Synfacts 2022; 18(08): 0927
DOI: 10.1055/s-0041-1737698
Peptide Chemistry

Palladium/Copper-Catalyzed Synthesis of α-Alkenyl α-Amino Acids from 2-Fluoro-1,3-dienes

Contributor(s):
Hisashi Yamamoto
,
Tomohiro Hattori
Yu H, Zhang Q, Zi W. * Nankai University, Tianjin, and Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, P. R. of China
Synergistic Pd/Cu-Catalyzed Enantioselective Csp2–F Bond Alkylation of Fluoro-1,3-Dienes with Aldimine Esters.

Nat. Commun. 2022;
13: 2470
DOI: 10.1038/s41467-022-30152-7
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Key words

palladium catalysis - copper catalysis - bimetal catalysis - aldimines - fluorodienes - alkenyl amino acids

Significance

α-Alkenyl α-amino acids have attracted significant attention because of their potential bioactivities. The authors have developed synergistic Pd- and Cu-catalyzed enantioselective alkylation of 2-fluoro-1,3-dienes with aldimine esters to afford α-alkenyl α-amino acids.


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Comment

The enantioselective C(sp2)–F bond alkylation of 2-fluoro-1,3-dienes with aldimine esters proceeded smoothly through Pd/Cu catalysis to afford the corresponding α-alkenyl α-amino acids in high yields and excellent enantiopurities. Moreover, the products could be subjected to further transformations, such as cyclization.


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Publication History

Article published online:
18 July 2022

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