New Catalytic Variant Of A Nearly 90-Year-Old Reaction Developed

A new catalytic and highly selective version of a chemical reaction first discovered in 1937 has been developed by the Smith group at the University of St Andrews.

The Sommelet–Hauser rearrangement allows chemists to reorganise atoms within a molecule and form new carbon–carbon bonds, producing valuable amine-containing chiral compounds. Chiral molecules are asymmetric or non-superimposable on their mirror image. Each side is different, existing in “right hand” and “left hand” forms. Often only one of these “handed” forms has the desired chemical or biological activity, while the other may have unwanted side effects.

Previous methods to control this reaction required a source of molecular “handedness” to be built into the starting material. The new approach instead uses a small amount of an organic catalyst to control the reaction, achieving selectivity for the formation of one-handed form of the products in up to a 98:2 ratio.

The method provides access to non-natural amino-acid derivatives that can be used as building blocks for making more diverse molecules. The work, carried out with collaborators at Oregon State University, also provides new insight into how this historic reaction takes place. It has been published in the Journal of the American Chemical Society. See more details here: https://doi.org/10.1021/jacs.6c04476