Beilstein J. Org. Chem.2013,9, 1751–1756, doi:10.3762/bjoc.9.202
Dhananjayan Vasu Samir Kundlik Pawar Rai-Shung Liu Department of Chemistry, National Tsing Hua University, Hsinchu, 30013, Taiwan (ROC) 10.3762/bjoc.9.202 Abstract 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.
Keywords: allenyl acetals; 5-alkylidenecyclopent-2-en-1-ones; cyclization; gold catalysis; Introduction
Gold-catalyzed cyclization/cycloaddition reactions [1][2][3][4][5] are useful synthetic methods to construct complicated carbo- and
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Graphical Abstract
Scheme 1:
Reported cascade reactions on allenyl acetals.