The catalytic tandem oxidation/benzilic ester rearrangement (BER): insights into reaction mechanism and stereoselectivity

This Letter describes an expeditious regiospecific and stereoselective approach to tertiary α-hydroxyesters via a simple one pot tandem catalytic oxidation/benzilic ester rearrangement of acyclic α-hydroxyketone substrates. Mechanistic studies confirming the regioselective nature of this reaction are discussed, including some insights into the nature of the stereoselectivity encountered in this reaction.