Gold-catalyzed cyclization of allenyl acetal derivatives

D Vasu, SK Pawar, RS Liu

Index: Vasu, Dhananjayan; Pawar, Samir Kundlik; Liu, Rai-Shung Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1751 - 1756

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Citation Number: 2

Abstract

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 ...