Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 3, Pages 1399-1405Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4028006
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Funding
- Berzelius Center EXSELENT
- Swedish Research Council
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Cycloisomerization of various gamma-acetylenic acids to their corresponding gamma-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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