Saturated heterocycles are prevalent in numerous therapeutics and bioactive natural products. To access new chemical space and function, many methods for the peripheral functionalization of these structures have been developed. Comparatively fewer methods are known for their skeletal remodeling, which could significantly enhance their diversification. We describe a visible light-mediated ring contraction of α-acylated saturated heterocycles. This unconventional transformation is orthogonal to traditional ring contractions, and is compatible with piperidine, morpholine, thiane, tetrahydropyran, and tetrahydroisoquinoline derivatives. The success of this light-mediated molecular editing strategy rests on reactivity differences between photoreactive ketone groups in unique chemical environments.

Molecular editing of saturated heterocyclic frameworks enabled by photo mediated ring contraction

ACS Fall 2021

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