1599447-18-3Relevant articles and documents
Developing the Scope of O→C Aryl Migrations: Exploring Amide Substrates as Potential Precursors for Asymmetric Reactions
Ameen, Dana,Snape, Timothy J.
, p. 1925 - 1934 (2015/10/05)
A new and mild method for the production of diasteromerically enriched α-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. A mild O→C aryl migration (Truce-Smiles rearrangement reaction) has been expanded to include amides as precursors, and it has been shown that the product ratios are dependent on the structure of the starting amides. Chiral auxiliaries have been incorporated in attempts to make the rearrangement asymmetric and modest diastereoselectivities were obtained.
