ArticleNature communications2018
Radical asymmetric intramolecular α-cyclopropanation of aldehydes towards bicyclo[3.1.0]hexanes containing vicinal all-carbon quaternary stereocenters.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Spatial Control Over Tether-Tunable Coordination on Palladium for Divergent Synthesis of Bicyclo[n.1.0]alkanes via Oxidative Cyclopropanation of Enynes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- PhAngewandte Chemie (International ed. in English) · 2025Article
- Enantioselective intramolecular cyclopropanation via a cationic sulfoxonium-Rh-carbene.Nature communications · 2025Article
- Merging SOMO activation with transition metal catalysis: Deoxygenative functionalization of amides to β-aryl amines.Science advances · 2025Article
- 1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls.Chemical science · 2024Article
- Recent Advances in the Enantioselective Radical Reactions.Molecules (Basel, Switzerland) · 2023Review
- One-Pot Synthesis of Difluorobicyclo[1.1.1]pentanes from α-Allyldiazoacetates.Organic letters · 2023Article
- Cu(ii)-mediated direct intramolecular cyclopropanation of distal olefinic acetate: access to cyclopropane-fused γ-lactones.Chemical science · 2023Article
- One-Pot Synthesis of α-Alkyl Styrene Derivatives.ACS omega · 2021Article
- Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.Journal of the American Chemical Society · 2021Article
- Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.Molecules (Basel, Switzerland) · 2021Article
- Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.Chemical science · 2020Review
- Direct use of 1,3-dienes for the allylation of ketonesRSC advances · 2020Article
- Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.Chemical science · 2019Article
- Chiral cyclopentadienyl RhChemical science · 2019Article
- Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover.Journal of the American Chemical Society · 2018Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of a general catalytic method for the direct and stereoselective construction of cyclopropanes bearing highly congested vicinal all-carbon quaternary stereocenters remains a formidable challenge in chemical synthesis. Here, we report an intramolecular radical cyclopropanation of unactivated alkenes with simple α-methylene group of aldehydes as C1 source via a Cu(I)/secondary amine cooperative catalyst, which enables the single-step construction of bicyclo[3.1.0]hexane skeletons with excellent efficiency, broad substrate scope covering various terminal, internal alkenes as well as diverse (hetero)aromatic, alkenyl, alkyl-substituted geminal alkenes. Moreover, this reaction has been successfully realized to an asymmetric transformation, providing an attractive approach for the construction of enantioenriched bicyclo[3.1.0]hexanes bearing two crucial vicinal all-carbon quaternary stereocenters with good to excellent enantioselectivity. The utility of this method is illustrated by facile transformations of the products into various useful chiral synthetic intermediates. Preliminary mechanistic studies support a stepwise radical process for this formal [2 + 1] cycloaddition.
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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.