ArticleACS catalysis2018
Catalytic Cyclopropanol Ring Opening for Divergent Syntheses of γ-Butyrolactones and δ-Ketoesters Containing All-Carbon Quaternary Centers.
Article in ACS catalysis, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed, 92 citations in OpenAlex.
- Chemoselectively Functionalized Ketoesters by Halogenative C-C Bond Cleavage of Cyclic Diketones.Molecules (Basel, Switzerland) · 2026Article
- α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.ChemistryOpen · 2024Review
- Asymmetric β-arylation of cyclopropanols enabled by photoredox and nickel dual catalysis.Chemical science · 2022Article
- Palladium-catalyzed selective C-C bond cleavage and stereoselective alkenylation between cyclopropanol and 1,3-diyne: one-step synthesis of diverse conjugated enynes.Chemical science · 2022Article
- A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones.International journal of molecular sciences · 2021Review
- Copper-Catalyzed Decarboxylative Functionalization of ConjugatedACS catalysis · 2020Article
- Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones.Chemical science · 2020Article
- Nickel-catalyzed reductive coupling of homoenolates and their higher homologues with unactivated alkyl bromides.Nature communications · 2020Article
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Authors and funding
4 authors at 1 institution in 1 country.
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Abstract
Catalytic ring opening cross coupling reactions of strained cyclopropanols have been useful for the syntheses of various β-substituted carbonyl products. Among these ring opening cross coupling reactions, the formation of α,β-unsaturated enone byproducts often competes with the desired cross coupling processes and has been a challenging synthetic problem to be addressed. Herein, we describe our efforts in developing divergent syntheses of a wide range of γ-butyrolactones and δ-ketoesters containing all-carbon quaternary centers via copper-catalyzed cyclopropanol ring opening cross couplings with 2-bromo-2,2-dialkyl esters. Our mechanistic studies reveal that unlike the previously reported cases, the formation of α,β-unsaturated enone intermediates is actually essential for the γ-butyrolactone synthesis and also contributes to the formation of the δ-ketoester product. The γ-butyrolactone synthesis is proposed to go through an intermolecular radical conjugate addition to the in situ generated α,β-unsaturated enone followed by an intramolecular radical cyclization to the ester carbonyl double bond. The reactions are effective to build all-carbon quaternary centers and have broad substrate scope.
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