ArticleAngewandte Chemie (International ed. in English)2020
Highly Regioselective Addition of Allylic Zinc Halides and Various Zinc Enolates to [1.1.1]Propellane.
Article in Angewandte Chemie (International ed. in English), 2020. 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.
- Propellane-free access to bicyclo[1.1.1]pentanes.Nature communications · 2026Review
- Bicyclo[1.1.1]pentane Ketones via Friedel-Crafts Acylation.The Journal of organic chemistry · 2026Article
- Synthesis of Diverse Glycosyl Bicyclo[1.1.1]pentanes Enabled by Electrochemical Functionalization of [1.1.1]Propellane.Journal of the American Chemical Society · 2025Article
- Highly Functional Allyl-Bicyclo[1.1.1]pentane Synthesis by Radical-Initiated Three-Component Stereoselective Allylation.JACS Au · 2025Article
- α-Amino bicycloalkylation through organophotoredox catalysis.Chemical science · 2024Article
- Expanding the Frontier of Linear Drug Design: Cu-Catalyzed CAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations.Nature synthesis · 2024Article
- 2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring.Nature chemistry · 2023Article
- Review
- A General and Practical Route to Functionalized Bicyclo[1.1.1]Pentane-Heteroaryls Enabled by Photocatalytic Multicomponent Heteroarylation of [1.1.1]Propellane.Angewandte Chemie (International ed. in English) · 2023Article
- Nickel-Mediated Alkyl-, Acyl-, and Sulfonylcyanation of [1.1.1]Propellane.Chem catalysis · 2023Article
- One step synthesis of unsymmetrical 1,3-disubstituted BCP ketonesChemical science · 2022Article
- General and Practical Route to Diverse 1-(Difluoro)alkyl-3-aryl Bicyclo[1.1.1]pentanes Enabled by an Fe-Catalyzed Multicomponent Radical Cross-Coupling Reaction.ACS catalysis · 2022Article
- Exploiting the spNature chemistry · 2022Article
- A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes.Angewandte Chemie (International ed. in English) · 2022Article
- Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- 1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics forProceedings of the National Academy of Sciences of the United States of America · 2021Article
- Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanesChemical science · 2021Article
- Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates.Chemical science · 2021Article
- Highly Regioselective Addition of Allylic Zinc Halides and Various Zinc Enolates to [1.1.1]Propellane.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
4 authors.
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Abstract
We report a range of highly regioselective openings of [1.1.1]propellane with various allylic zinc halides, as well as zinc enolates of ketones, esters and nitriles. The resulting zincated bicyclopentanes (BCPs) were trapped with a range of electrophiles including acyl chlorides, sulfonothioates, hydroxylamino benzoates, tosyl cyanide as well as aryl and allyl halides, generating highly functionalized BCP-derivatives. The unusually high regioselectivity of these reactions has been rationalized using DFT calculations. A bioisostere of the synthetic opioid pethidine was prepared in 95 % yield in one step using this method.
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