AuCl < inf > 3 < /inf > /AgSbF < inf > 6 < /inf > -catalyzed rapid epoxide to carbonyl rearrangement

Abstract

An efficient epoxide to carbonyl rearrangement using catalytic AuCl 3/AgSbF 6 has been presented. The reactions are fast and high yielding. β-Hydrogen migration takes place exclusively when hydrogen and methyl or substituted methyl groups are present at β-carbon of epoxide. When phenyl/acetyl/benzoyl and hydrogen are available at same carbon atom, migration of the former is preferred over the latter. © 2012 Elsevier Ltd. All rights reserved.