New symmetry-breaking method opens way for bioactive compounds

Many chemical molecules can exist in nature together with their mirror counterparts; like hands, two compounds can be made up of the same atoms in the same overall structure but in opposite orientations, i.e. left-handed and right-handed. This phenomenon of symmetry is called "chirality", and can give mirror counterparts ("enantiomers") entirely different chemical properties. A famous and tragic example of chirality is thalidomide, which was originally sold as a mixture of both enantiomers. The problem was that one was a harmless sedative and the other highly toxic to fetuses, resulting in disturbing congenital deformities. So today it has become imperative to synthesize compounds with what is known as high "optical purity", which is a measurement of chiral purity: the degree to which a sample contains one enantiomer in greater amounts than the other. But because enantiomers have very small structural differences and identical stability, synthesizing one over the other is a very challenging task. One way to do this is what chemists call "desymmetrization" of a non-chiral compound that is similar to the target molecule. This involves modifying a molecule so that it loses the symmetry elements that prevented it to be chiral.Researchers at Jérôme Waser's Laboratory of Catalysis and Organic Synthesis at EPFL have now developed a new desymmetrization strategy to access chiral building blocks containing urea sub-structures.