ArticleJournal of the American Chemical Society2025
Catalytic Asymmetric Synthesis of Axially Chiral Methylenecyclopropanes.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Deoxygenative Single-Carbon Atom Transfer: Accessing Strained Carbocycles From Alkenes and Aldehydes With Designer Dual-Functional Reagent.Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective Synthesis of Axially Chiral Spiro[3.3]heptanes by Site-Selective C-H Functionalization.ACS catalysis · 2026Article
- Deuterated Cyclopropanation of Alkenes by Iron Catalysis.Organic letters · 2026Article
- Bulky alkali metal cations enabled highly efficient iridium-catalyzed asymmetric hydrogenation for C-N axial chiralityChemical science · 2026Article
- Catalytic asymmetric construction of remote P or other heteroatom (Si/S) stereogenic axially chiral scaffolds.Chemical science · 2026Article
- Application of Asymmetric Catalysis in theJournal of the American Chemical Society · 2025Article
- Divergent Transformations of Cobaltacyclobutenes Generated from [2 + 2]-Cycloadditions of Vinylidenes and Alkynes.ACS catalysis · 2025Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Atropisomeric compounds and 1,3-disubstituted allenes are the most common examples of axial chirality in organic chemistry. However, there are less explored classes of axially chiral molecules that may also hold significant value in asymmetric synthesis. Here, we report a catalytic asymmetric synthesis of axially chiral methylenecyclopropanes by a [2 + 1]-cycloaddition of an alkene and a vinylidene equivalent. Computational models provide a rationale for the origin of asymmetric induction and indicate that key elements of stereocontrol differ from catalytic enantioselective cyclopropanation reactions using carbenes. Methylenecyclopropanes participate in a broad range of axial-to-central chirality transfer reactions that take advantage of addition to the alkene or ring-opening of the strained three-membered ring.
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Registered trials
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