New elements in the gold(I)-catalyzed cycloisomerization of enynyl ester derivatives embedding a cyclohexane template

The gold-catalyzed cycloisomerization of enynyl esters bearing a cyclohexyl template has been studied and has been shown to lead to two types of products arising from 1,2- vs. 1,3-O-acyl-migration. Results have shown to be dependent on the nature of the solvent, the catalysts, the migrating group, the stereochemistry of the starting diastereomer as well as the alkene partner. This set of findings confirms the intricate nature of the golden carousel of propargylic acetates. (C) 2010 Elsevier B.V. All rights reserved.