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Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

G. Eray Akpınar, Melih Kuş, Muhammed Uçuncu, Erman Karakuş and Levent Artok*

*Department of Chemistry, Faculty of Science, Izmir Institute of Technology, Urla 35430, Izmir, Turkey, Email: leventartokiyte.edu.tr

G. E. Akpınar, M. Kuş, M. Uçncu, E. Karakuş, L. Artok, Org. Lett., 2011, 13, 748-751.

DOI: 10.1021/ol102989q (free Supporting Information)


Abstract

Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of CO and an alcohol gives vinylallenyl esters with an exclusively E-configuration in high yields. The unreactivity of E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

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Regio- and Stereoselective Synthesis of 2,3,5-Trienoates by Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Carbonates

E. Ş. Karagöz, M. Kuş, G. E. Akpınar, L. Artok, J. Org. Chem., 2014, 79, 9222-9230.


Key Words

Allenes, Dienes, Unsaturated Esters


ID: J54-Y2011-0380