Cycloisomerization of Acetylenic Acids to γ‑Alkylidene Lactones using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam

Cycloisomerization of various γ-acetylenic acids to their corresponding γ-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well as internal alkynes were cyclized in high to...

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Veröffentlicht in:Journal of organic chemistry 2014-02, Vol.79 (3), p.1399-1405
Hauptverfasser: Nagendiran, Anuja, Verho, Oscar, Haller, Clémence, Johnston, Eric V, Bäckvall, Jan-E
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Sprache:eng
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Zusammenfassung:Cycloisomerization of various γ-acetylenic acids to their corresponding γ-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well as internal alkynes were cyclized in high to excellent yields within 2–24 h under mild reaction conditions. The protocol exhibited high regio- and stereoselectivity, favoring the exo-dig product with high Z selectivity. Moreover, the catalyst displayed excellent stability under the employed reaction conditions, as demonstrated by its good recyclability and low leaching.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo4028006