Developing the Scope of O-C Aryl Migrations: Exploring Amide Substrates as Potential Precursors for Asymmetric Reactions

A new and mild method for the production of diasteromerically enriched -aryl carbonyl compounds has been achieved. Although only modest diastereoselectivies are observed, they demonstrate the potential of the method for further optimisation. It also appears that reactions that proceed through a five-membered spirocyclic transition state rearrange, whereas those proceeding through a six-membered transition state do not, but stop at the diaryl ether stage.