ArticleAngewandte Chemie (International ed. in English)2021
Strain-Release Driven Spirocyclization of Azabicyclo[1.1.0]butyl Ketones.
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 20 papers.
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Who cites it
20 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
- Modular Access toJournal 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
- Beyond Strain Release: Delocalization-Enabled Organic Reactivity.The Journal of organic chemistry · 2024Article
- Access to 3-Azetidines via Halogenation of Titanacyclobutanes.Advanced synthesis & catalysis · 2024Article
- Article
- 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
- Total synthesis of the antibacterial polyketide natural product thailandamide lactone.Chemical science · 2022Article
- Photoredox-catalyzed C-C bond cleavage of cyclopropanes for the formation of C(spNature communications · 2022Article
- Strain-Release-Driven Friedel-Crafts Spirocyclization of Azabicyclo[1.1.0]butanes.Angewandte Chemie (International ed. in English) · 2022Article
- Strain-Release Driven Spirocyclization of Azabicyclo[1.1.0]butyl Ketones.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Due to their intrinsic rigidity, three-dimensionality and structural novelty, spirocyclic molecules have become increasingly sought-after moieties in drug discovery. Herein, we report a strain-release driven synthesis of azetidine-containing spirocycles by harnessing the inherent ring strain of the azabicyclo[1.1.0]butane (ABB) fragment. Novel ABB-ketone precursors bearing silyl-protected alcohols were synthesized in a single step and shown to engage in electrophile-induced spirocyclization-desilylation reactions. Primary, secondary and tertiary silyl ethers were effectively transformed into a library of new spiro-azetidines, with a range of substituents and ring sizes. In addition, the products are generated with synthetically useful ketone and protected-amine functional groups, which provides the potential for further elaboration and for this chemistry to be utilized in the rapid assembly of medicinally relevant compounds.
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