An unusual gold-catalyzed rearrangement of α-hydroxy epoxides

A novel gold-catalyzed rearrangement of alpha-hydroxy epoxides has been investigated. The reaction proceeds efficiently under mild conditions to afford unsymmetrical 1,5 or 1,6-diketones and monoketones in moderate to high yields. The selective formation of the two products could be controlled by substituents and ring strain. [GRAPHICS] Crown Copyright (c) 2009 Published by Elsevier B.V. All rights reserved.