ArticleJournal of the American Chemical Society2024
Enantioselective Potassium-Catalyzed Wittig Olefinations.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Enantioselective Synthesis of Axially Chiral Spiro[3.3]heptanes by Site-Selective C-H Functionalization.ACS catalysis · 2026Article
- Catalytic asymmetric construction of remote P or other heteroatom (Si/S) stereogenic axially chiral scaffolds.Chemical science · 2026Article
- Catalytic Asymmetric Synthesis of Axially Chiral Methylenecyclopropanes.Journal of the American Chemical Society · 2025Article
- Rh(I)-Catalyzed Modular Synthesis of Axially Chiral Alkylidene Azacycloalkanes.ACS central science · 2025Article
- Palladium-catalyzed enantioselective β-hydride elimination for the construction of remote stereocenters.Nature communications · 2025Article
- Ligand-controlled regiodivergent arylation of aryl(alkyl)alkynes and asymmetric synthesis of axially chiral 9-alkylidene-9,10-dihydroanthracenes.Nature communications · 2024Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
We report asymmetric potassium-isothiourea-boronate-catalyzed Wittig olefinations of 4-substituted cyclohexanones with non-stabilized phosphorus ylides to afford highly enantioenriched axially chiral alkenes. The optimal catalyst features an unusual macrocyclic amide-potassium-boronate chelate. Kinetic and spectroscopic analyses are consistent with a Lewis acid mechanism for the catalytic olefination that results in the formation of the oxaphosphetane adduct under cryogenic conditions. Thermal fragmentation of the oxaphosphetane to the alkene product occurs after the reaction is complete. Computational studies indicate that cycloaddition proceeds via a stepwise mechanism involving enantiodetermining polar 1,2-addition to afford an intermediate potassium betaine complex.
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Registered trials
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