Regio- and Stereoselective Synthesis of 2,3,5-Trienoates by Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Carbonates
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BRONZE
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Yes
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Abstract
Palladium-catalyzed carbonylation of 2,4-enyne carbonates in an alcohol and under balloon pressure of CO proceeds through 1,5-substitution to yield (E)-2,3,5-trienoates. The olefin geometry of the substrate is important to control the overall stereochemistry of this alkoxycarbonylation method. The reaction proceeds through successive formation of π-allylpalladium with an R3 group oriented syn and σ-allenyl palladium complexes.
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Keywords
Carbonates, Group-oriented, Stereochemistry, Palladium compounds, Stereoselective synthesis, Palladium compounds, Molecular Structure, Group-oriented, Stereoselective synthesis, Carbonates, Stereoisomerism, Alkenes, Catalysis, Stereochemistry, Alcohols, Palladium
Fields of Science
01 natural sciences, 0104 chemical sciences
Citation
Karagöz, E.Ş., Kuş, M., Akpınar, G.E., and Artok, L. (2014). Regio- and stereoselective synthesis of 2,3,5-trienoates by palladium-catalyzed alkoxycarbonylation of conjugated enyne carbonates. Journal of Organic Chemistry, 79(19), 9222-9230. doi:10.1021/jo5014993
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20
Volume
79
Issue
19
Start Page
9222
End Page
9230
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Scopus : 21
PubMed : 2
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