Gold-catalyzed cyclization of allenyl acetal derivatives.
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.
Department of Chemistry, National Tsing Hua University, Hsinchu, 30013, Taiwan (ROC).
Dhananjayan
D
Vasu
Samir Kundlik
SK
Pawar
Rai-Shung
RS
Liu
5-alkylidenecyclopent-2-en-1-ones; allenyl acetals; cyclization; gold catalysis