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

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Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden
*E-mail: [email protected] (E.V.J.); [email protected] (J.-E.B.).
Cite this: J. Org. Chem. 2014, 79, 3, 1399–1405
Publication Date (Web):January 15, 2014
https://doi.org/10.1021/jo4028006
Copyright © 2014 American Chemical Society

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    Abstract

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    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.

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