ArticleJournal of the American Chemical Society2018
Arynes and Cyclic Alkynes as Synthetic Building Blocks for Stereodefined Quaternary Centers.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Mechanisms of Kobayashi eliminations for the generation of highly strained arynes, cyclic cumulenes, and anti-Bredt olefins.Chemical science · 2025Article
- Geometric distortion as an enabling tool for organic synthesis.Nature synthesis · 2025Article
- Generation of Quaternary Carbons in Cycloalkanones and Lactones with Arynes through a Domino Process.The Journal of organic chemistry · 2024Article
- Evaluation of Retro-Aldol vs Retro-Carbonyl-Ene Mechanistic Pathways in a Complexity-Generating C-C Bond Fragmentation.Organic letters · 2024Article
- Sulfonium-based precise alkyl transposition reactions.Science advances · 2023Article
- Asymmetric reactions involving aryne intermediates.Nature reviews. Chemistry · 2023Review
- Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions.Chemical science · 2023Article
- α-C(spNatural products and bioprospecting · 2021Review
- Review
- Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination.Organic letters · 2021Article
- α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation.Angewandte Chemie (International ed. in English) · 2020Article
- α-Arylation of Carbonyl Compounds through Oxidative C-C Bond Activation.Angewandte Chemie (International ed. in English) · 2019Article
- Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres.Chemical science · 2019Article
- Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study.Molecules (Basel, Switzerland) · 2019Article
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7 authors.
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Abstract
We report a facile method to synthesize stereodefined quaternary centers from reactions of arynes and related strained intermediates using β-ketoester-derived substrates. The conversion of β-ketoesters to chiral enamines is followed by reaction with in situ generated strained arynes or cyclic alkynes. Hydrolytic workup provides the arylated or alkenylated products in enantiomeric excesses as high as 96%. We also describe the one-pot conversion of a β-ketoester substrate to the corresponding enantioenriched α-arylated product. Computations show how chirality is transferred from the N-bound chiral auxiliary to the final products. These are the first theoretical studies of aryne trapping by chiral nucleophiles to set new stereocenters. Our approach provides a solution to the challenging problem of stereoselective β-ketoester arylation/alkenylation, with formation of a quaternary center.
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