ArticleAngewandte Chemie (International ed. in English)2021
Divergent, Strain-Release Reactions of Azabicyclo[1.1.0]butyl Carbinols: Semipinacol or Spiroepoxy Azetidine Formation.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- 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
- Photochemical thiocarbonyl difluoride generation enables azetidine synthesis.Nature communications · 2026Article
- Novel Sulfonium Reagents for the Modular Synthesis of Spiro[2.3]Hexanes and Heteroatom-Containing Analogues: Synthesis, Application, and Evaluation as Bioisosteres.Angewandte Chemie (International ed. in English) · 2026Article
- HFIP-assisted Brønsted acid-catalyzed ring opening of 1-azabicyclo[1.1.0]butane to access diverse C3-quaternary aza-azetidines and indole-azetidines.Nature communications · 2025Article
- Modular Access toJournal of the American Chemical Society · 2025Article
- Fused-Linked and Spiro-Linked N-Containing Heterocycles.International journal of molecular sciences · 2025Review
- Enantiocontrolled Azetidine Library Synthesis via Strain-Release Functionalization of 1-Azabicyclobutanes.Journal of the American Chemical Society · 2025Article
- 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
- Harnessing Oxetane and Azetidine Sulfonyl Fluorides for Opportunities in Drug Discovery.Journal of the American Chemical Society · 2024Article
- Stereoselective polar radical crossover for the functionalization of strained-ring systems.Communications chemistry · 2024Article
- 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 (International ed. in English) · 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
- Synthesis of Dihydropyridine Spirocycles by Semi-Pinacol-Driven Dearomatization of Pyridines.Organic letters · 2023Article
- Four-Component Strain-Release-Driven Synthesis of Functionalized Azetidines.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
3 authors.
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Abstract
The azetidine moiety is a privileged motif in medicinal chemistry and new methods that access them efficiently are highly sought after. Towards this goal, we have found that azabicyclo[1.1.0]butyl carbinols, readily obtained from the highly strained azabicyclo[1.1.0]butane (ABB), can undergo divergent strain-release reactions upon N-activation. Treatment with trifluoroacetic anhydride or triflic anhydride triggered a semipinacol rearrangement to give keto 1,3,3-substituted azetidines. More than 20 examples were explored, enabling us to evaluate selectivity and the migratory aptitude of different groups. Alternatively, treatment of the same alcohols with benzyl chloroformate in the presence of NaI led to iodohydrin intermediates which gave spiroepoxy azetidines upon treatment with base. The electronic nature of the activating agent dictates which pathway operates.
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