JACS Au· 2026Q1
Synthesis of 15N-Labeled Complex Saturated N -Heterocycles via Late-Stage Carbonyl-to-Nitrogen Swap
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- 2026year
Short summary
A new method converts complex cyclic ketones into 15N-enriched saturated heterocycles using a methylsulfonyl-based azonation reagent that enables late-stage skeletal modification.
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Key points
- A late-stage carbonyl-to-15N skeletal modification strategy converts cyclic ketones into 15N-enriched saturated heterocycles.
- A methylsulfonyl-based 15N-labeled azonation reagent enables the transformation by cleaving C-C bonds while suppressing overoxidation.
- The reaction shows broad substrate scope and tolerates diverse functional groups.
- The method is applicable for late-stage skeletal modifications of complex natural products and drug-like molecules.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Efficient construction of 15N-labeled complex saturated N-heterocycles remains a substantial challenge. Here we report a late-stage carbonyl-to-15N skeletal modification strategy that converts complex cyclic ketones directly into 15N-enriched saturated heterocycles. This transformation is enabled by a methylsulfonyl-based 15N-labeled azonation reagent that suppresses unwanted overoxidation without compromising the desired C–C bond cleavage pathway. The reaction exhibits a broad substrate scope and tolerates a wide range of functional groups, serving as an effective tool for late-stage skeletal modifications of complex natural products and drug-like molecules. Mechanistic insights on the sequential double C–C activation events have been elucidated by preliminary computational studies.
The authors' abstract, as published at the source. JACS Au, 2026 · DOI ↗
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Field: Pharmaceutical Science
Pharmaceutical SciencePharmacology, Toxicology and Pharmaceutics