Advanced Science· 2026Q1
Lewis Acid‐Catalyzed Strain‐Enabled (3+3) Annulation of Bicyclo[1.1.0]Butanes With Indolylalcohols: Synthesis of Indole‐Fused Aza‐Bicyclo[3.1.1]Heptanes
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- 2026year
Short summary
A Lewis acid-catalyzed reaction efficiently synthesizes indole-fused aza-bicyclo[3.1.1]heptanes by annulating strained bicyclo[1.1.0]butanes with indolyl alcohols.
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Key points
- Developed a Lewis acid-catalyzed formal (3+3) annulation of bicyclo[1.1.0]butanes with indolyl alcohols.
- Synthesizes indole-fused aza-bicyclo[3.1.1]heptanes, which are rigid, sp3-rich scaffolds.
- Reaction proceeds under mild conditions and tolerates a broad range of functional groups.
- Mechanistic studies indicate a stepwise pathway involving Lewis acid activation and strain-release driven bond formation.
AI-generated from the title and abstract; the full text is not read.
Abstract
ABSTRACT Strain release has long inspired the discovery of unique reactivity, enabling diverse synthetically valuable transformations. Bicyclo[1.1.0]butanes (BCBs), due to their high ring strain, have emerged as versatile building blocks for constructing complex bicyclic architectures. Herein, we report a Lewis acid‐catalyzed formal (3 + 3) annulation of BCBs with indolyl alcohols, providing rapid access to indole‐fused aza‐bicyclo[3.1.1]heptanes. The reaction proceeds under mild conditions, tolerates a broad range of functional groups, and delivers rigid, sp 3 ‐rich scaffolds efficiently. Mechanistic studies, including control experiments and computational analysis, indicate a stepwise pathway in which Lewis acid activation of indolyl alcohols generates reactive intermediates, while strain‐release of BCBs drives C–C bond formation, followed by C–N bond formation via ring expansion to furnish the fused Aza‐bicyclic products.
The authors' abstract, as published at the source. Advanced Science, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry