ArticleAngewandte Chemie (International ed. in English)2022
Strain-Release-Driven Friedel-Crafts Spirocyclization of Azabicyclo[1.1.0]butanes.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 42 citations in OpenAlex.
- Modular synthesis of functionalized azetidines through visible-light copper-catalyzed carboamination of 1,3-dienes with azabicyclo[1.1.0]butanes.Chemical science · 2026Article
- Single-carbon insertion enables conversion of cyclopropenes into cyclobutenes: access to oxaspiro[2.3]hexenes.Chemical science · 2026Article
- Strain Release of 1-Azabicyclo[1.1.0]butanes as a Gateway to Highly Functionalized Azetidines: New Strategies and Structural Motifs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Regio- and Stereoselective Deprotonation and Functionalization of Strained 1-Aza[n.1.0]bicycles.Journal of the American Chemical Society · 2026Article
- Lewis Acid Catalyzed Dual Strain-Release Platform for Transforming Azabicyclo[1.1.0]butanes into Functionalized Azetidines with Donor-Acceptor(D-A) Cyclopropanes and Bicyclo[1.1.0]butanes.Organic letters · 2026Article
- Triplet Energy Transfer-Driven Intermolecular [2+2] Photocycloaddition of Acyclic Imines and Indoles: Facile Access to Azetidine-Fused Indolines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Modular Access toJournal of the American Chemical Society · 2025Article
- Divergent Synthesis of 1-Azabicyclo[n.1.1]alkane Bioisosteres via Photoinduced Palladium Catalysis.Journal of the American Chemical Society · 2025Article
- Fused-Linked and Spiro-Linked N-Containing Heterocycles.International journal of molecular sciences · 2025Review
- Synthesis of 2-(Trifluoromethyl)Azetidines by Strain-Release Reactions of 2-(Trifluoromethyl)-1-Azabicyclo[1.1.0]Butanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- A focus on 1-azahomocubane: the new kid on the block.Chemical science · 2023Article
- Synthesis and Applications of Bicyclo[1.1.0]butyl and Azabicyclo[1.1.0]butyl Organometallics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Review
- Expedient synthesis of spiro[3.3]heptan-1-ones via strain-relocating semipinacol rearrangements.Tetrahedron · 2023Article
- Strain-Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ-Bond Nucleopalladation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Strain-Release Driven Epoxidation and Aziridination of Bicyclo[1.1.0]butanes via Palladium Catalyzed σ-Bond Nucleopalladation.Angewandte Chemie (International ed. in English) · 2023Article
- Four-Component Strain-Release-Driven Synthesis of Functionalized Azetidines.Angewandte Chemie (International ed. in English) · 2022Article
- Strain-Release-Driven Friedel-Crafts Spirocyclization of Azabicyclo[1.1.0]butanes.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The identification of spiro N-heterocycles as scaffolds that display structural novelty, three-dimensionality, beneficial physicochemical properties, and enable the controlled spatial disposition of substituents has led to a surge of interest in utilizing these compounds in drug discovery programs. Herein, we report the strain-release-driven Friedel-Crafts spirocyclization of azabicyclo[1.1.0]butane-tethered (hetero)aryls for the synthesis of a unique library of azetidine spiro-tetralins. The reaction was discovered to proceed through an unexpected interrupted Friedel-Crafts mechanism, generating a highly complex azabicyclo[2.1.1]hexane scaffold. This dearomatized intermediate, formed exclusively as a single diastereomer, can be subsequently converted to the Friedel-Crafts product upon electrophilic activation of the tertiary amine, or trapped as a Diels-Alder adduct in one-pot. The rapid assembly of molecular complexity demonstrated in these reactions highlights the potential of the strain-release-driven spirocyclization strategy to be utilized in the synthesis of medicinally relevant scaffolds.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.