Carbonyl swapping converts cyclic ketones to saturated heterocycles

"Saturated heterocycles are privileged scaffolds in bioactive molecules, and accessing diverse heterocycles from a unified carbocycle offers a strategic alternative for constructing challenging structures."

"The method exhibits broad substrate scope and functional-group tolerance, enabling both accelerated target synthesis and late-stage diversification of bioactive molecules."

"Through electronically guided peroxy cleavage, the bis(aroylperoxy) ketal intermediate enables double CC bond scission of cyclic ketones, generating alkyl dichlorides as versatile handles."

A novel synthetic methodology allows the transformation of a single cyclic ketone into various saturated heterocycles. This is achieved through formal carbonyl replacement with heteroatoms via a bis(aroylperoxy) ketal intermediate. The method facilitates double CC bond scission of cyclic ketones, producing alkyl dichlorides that serve as versatile handles for incorporating nucleophiles. The approach demonstrates broad substrate scope and functional-group tolerance, enhancing target synthesis and late-stage diversification of bioactive molecules. Additionally, it combines CH oxidation with carbonyl replacement for constructing challenging heterocycles.

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