ArticleAngewandte Chemie (International ed. in English)2022
Four-Component Strain-Release-Driven Synthesis of Functionalized Azetidines.
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 14 papers.
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Who cites it
14 citing papers in PubMed.
- 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
- 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
- Enantioselective Synthesis of 2,3-Disubstituted Azetidines via Copper-Catalyzed Boryl Allylation of Azetines.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
- A modular synthesis of azetidines from reactive triplet imine intermediates using an intermolecular aza Paternò-Büchi reaction.Nature catalysis · 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
- Four-Component Strain-Release-Driven Synthesis of Functionalized Azetidines.Angewandte Chemie (International ed. in English) · 2022Article
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3 authors.
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Abstract
Despite the favorable properties that azetidine rings can engender on drug-compounds, methods for the diversity-oriented synthesis of azetidine-based structures are significantly underdeveloped. Herein, we report the successful realization of a multicomponent [1,2]-Brook rearrangement/strain-release-driven anion relay sequence and its application to the modular synthesis of substituted azetidines. The rapidity of the reaction, as confirmed by in situ infra-red spectroscopy, leverages the strain-release ring-opening of azabicyclo[1.1.0]butane to drive the equilibrium of the Brook rearrangement. The three electrophilic coupling partners, added sequentially to azabicyclo[1.1.0]butyl-lithium, could be individually varied to access a diverse compound library. The utility of this methodology was demonstrated in a 4-step synthesis of the EP2 receptor antagonist PF-04418948.
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