Ring Contraction of Saturated Heterocycles

Richmond Sarpong reports on the photomediated ring contraction of saturated heterocycles.

Skeletal editing, the precise manipulation of a molecule’s core scaffold, especially at the single atom level, is an emerging concept of importance in organic chemistry. Recent reports in this area have included nitrogen deletion, single-atom insertion, and ring contractions. Through a collaboration involving researchers at the University of California-Berkeley in Professor Richmond Sarpong’s laboratory and at the research labs of Merck & Co., Inc. Kenilworth, NJ, USA – known as MSD outside of the USA and Canada – a light-mediated ring contraction of saturated six-membered heterocycles to five-membered rings that relocates the heteroatom from an endocyclic to exocyclic position has been achieved. This academia/industry partnership started as part of the “Disruptive Chemistry” initiative at MSD – an effort focused on developing enabling chemical reactions of importance for industrial applications, including novel scaffold changes to precisely edit molecules.

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