Programmable Functionalizations of Tetramethylpiperidine N‑Oxyl (TEMPO)–Acrolein Linchpins Derived from Alkoxyallenes

Description

Ken S Lee and colleagues published a 2026 synthetic chemistry study turning simple alkoxyallenes into versatile three-carbon building blocks carrying a TEMPO group and an aldehyde, which they call linchpins. Allenes invite chemists to decorate all three carbons, but oxidation methods have relied on awkward reagents and produced unstable intermediates that cannot be stored or steered. Their route installs the two handles cleanly, yielding an intermediate reactable at each carbon in turn.

From these linchpins the team built a gallery of nitrogen- and oxygen-containing rings prized in drug discovery, including quinoxalines, imidazoles, oxazoles, and thiazoles. As a proof of the strategy's reach, they completed a short metal-free synthesis of the natural product clathrodin. The authors present the linchpin concept as a general platform: park a stable, multifunctional intermediate, then diverge into many scaffolds from one starting material rather than redesigning each route.

Catalog record

Source: https://europepmc.org/articles/PMC13281524