Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 1751-1756Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.202
Keywords
allenyl acetals; 5-alkylidenecyclopent-2-en-1-ones; cyclization; gold catalysis
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Funding
- National Science Council, Taiwan
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The gold-catalyzed transformation of allenyl acetals into 5-alkylidenecyclopent-2-en-1-ones is described. The outcome of our deuterium labeling experiments supports a 1,4-hydride shift of the resulting allyl cationic intermediates because a complete deuterium transfer is observed. We tested the reaction on various acetal substrates bearing a propargyl acetate, giving 4-methoxy-5-alkylidenecyclopent-2-en-1-ones 4 via a degradation of the acetate group at the allyl cation intermediate.
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