Synthesis of N -(4-Vinylidenetetrahydrofuran-2-yl)amides and Applications in Skeletal Rearrangement to 2,3-Dihydro-1 H -pyrrol-2-ols/Substituted Pyrroles and Bridged Bicyclic Scaffold Construction
Abstract
Advancing molecular complexity enhances biological activity and material functions, accelerating drug discovery. Thus, the synthesis of complex structures from simple precursors is crucial. A Lewis acid-catalyzed method to prepare polyfunctionalized N -(4-vinylidenetetrahydrofuran-2-yl)amides with a tetrasubstituted allene moiety from tertiary but-2-yne-1,4-diols and enamides is developed. Moreover, these complex structures can be transformed into 2,3-dihydro-1 H -pyrrol-2-ols and substituted pyrroles via gold-catalyzed skeletal rearrangement through O–N exchange of atoms and molecules as well as novel bridged bicyclic scaffolds via electrophilic addition/cyclization, offering a new strategy for rapidly accessing molecular complexity.
Fields of Study & Subjects
Synthesis and Characterization of Pyrroles
Catalytic Alkyne Reactions
Synthesis and Reactivity of Heterocycles
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 11
- Pages
- 3606–3611
- Publication date
- 6 March 2026
- Language
- EN