Stereoselective desymmetrizations: role of symmetry, stereofacial discrimination and steric effects

A stereoselective desymmetrization is a symmetry breaking synthetic operation and represents a powerful synthetic tool not only for the preparation of new chiral synthons or building blocks, but also for the applications in the target oriented synthesis, yielding enantiomerically enriched products. In this microreview, after a brief historical overview of the origin of the method, through representative examples that go back to the last six years, we describe the role of molecular symmetryand steric effectson the stereotopic and stereofacial discrimination mechanisms. The most effective procedures to perform a stereoselective desymmetrization of a non chiral symmetric compound by nonenzymatic or enzymatic methods are here presented.