Enantioselective Synthesis of γ-Hydroxyenones by Chiral Base-Catalyzed Kornblum DeLaMare Rearrangement

Abstract

A cinchona-alkaloid catalyzed asymmetric Kornblum DeLaMare rearrangement has been developed. Thus, enantioenriched 4-hydroxyenones are prepared from dienes by a two-step sequence involving photochemical dioxygenation and chiral base-catalyzed desymmetrization of the resulting endoperoxides.