Synthesis· 2026Q2
A Formal (3+2) Cycloaddition Strategy toward 2-aza-Norbornanes
- 9citations
- Q2SCImago
- 2026year
Short summary
A new photochemical method constructs 2-azanorbornane scaffolds from cyclopropylsulfonamides via a cascade radical cyclization initiated by Lewis acid-promoted ring opening.
AI-generated from the title and abstract; the full text is not read.
Key points
- A photochemical method constructs 2-azanorbornane scaffolds from cyclopropylsulfonamide derivatives.
- Lewis acid additives promote amine radical cation formation via single-electron transfer and cyclopropylamine ring opening.
- The process initiates a cascade radical cyclization sequence.
- The method allows substitution at all carbon centers and shows A1,3 stereocontrol for C3 substituted derivatives.
AI-generated from the title and abstract; the full text is not read.
Abstract
Reported herein is the development of a photochemical method which allows for the construction of 2-azanorbornane scaffolds from cyclopropylsulfonamide derivatives. Access to the amine radical cation of these species is promoted by a Lewis acid additive which enables the ring opening of the cyclopropylamine moiety to initiate a cascade radical cyclization sequence. Notably, the method allows access to substituted 2-azanorbornane derivatives at all possible carbon centers and A1,3 stereocontrol is observed for C3 substituted derivatives. Preliminary mechanistic investigations suggest an integral role for the Lewis acid additive in facilitating single-electron transfer and avoiding deleterious dealkylation of the starting material. Thus, this method constitutes a modular, mild, and operationally simple approach to privileged saturated aza-heterocycles.
The authors' abstract, as published at the source. Synthesis, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry