Gold-catalyzed cyclization of allenyl acetal derivatives.

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.

SUBMITTER: Vasu D 

PROVIDER: S-EPMC3778408 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature