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

Ezgi Şule Karagöz, Melih Kuş, Gürkan Eray Akpınar and Levent Artok*

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

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

DOI: 10.1021/jo5014993 (free Supporting Information)



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Abstract

Palladium-catalyzed alkoxycarbonylation of 2,4-enyne carbonates proceeds in an alcohol and under balloon pressure of CO through 1,5-substitution. The olefin geometry controls the overall stereochemistry of this alkoxycarbonylation method.

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

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


Key Words

carboxylation, allenes, dienes


ID: J42-Y2014