ArticleJournal of the American Chemical Society2021
α- and β-Functionalized Ketones from 1,3-Dienes and Aldehydes: Control of Regio- and Enantioselectivity in Hydroacylation of 1,3-Dienes.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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19 citing papers in PubMed, 69 citations in OpenAlex.
- Synthesis of 1,3-Dienes from Alkenes via Alkenyl Thianthrenium Salts.Journal of the American Chemical Society · 2026Article
- Enantioselective Syntheses of Secondary Alkylboronates via Asymmetric Regioselective Reduction of 1,3-Dienylboronates.Angewandte Chemie (International ed. in English) · 2026Article
- Construction of remote dual stereocenters by electrochemical cobalt-catalyzed enantioselective desymmetrization.Nature communications · 2026Article
- Ligand Effects in Regio- and Enantioselective Cobalt-Catalyzed Intramolecular [4+2]- and [2+2]-Cycloaddition Reactions of Unactivated 1,3-Diene-8-ynes and 1,3-Diene-8-enes.Angewandte Chemie (International ed. in English) · 2025Article
- Cyclopropylmethyl Boronic Esters as General Reagents in Transition-Metal Catalyzed Homoallylation Reactions.Journal of the American Chemical Society · 2025Article
- Iron-catalyzed three-component 1,2-azidoalkylation of conjugated dienesChemical science · 2025Article
- Stereoselective rhodium-catalyzed reaction of allenes with organoboronic reagents for diversified branched 1,3-alkadienes.Nature communications · 2024Article
- Ligand Effects in Carboxylic Ester- and Aldehyde-Assisted β-C-H Activation in Regiodivergent and Enantioselective Cycloisomerization-Hydroalkenylation and Cycloisomerization-Hydroarylation, and [2 + 2 + 2]-Cycloadditions of 1,6-Enynes.Journal of the American Chemical Society · 2024Article
- Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis.JACS Au · 2024Article
- CoH-catalyzed asymmetric remote hydroalkylation of heterocyclic alkenes: a rapid approach to chiral five-membered S- and O-heterocycles.Chemical science · 2024Article
- Dienes as Versatile Substrates for Transition Metal-Catalyzed Reactions.Angewandte Chemie (International ed. in English) · 2024Review
- Cobalt-Catalyzed Enantioselective Hydroboration of α-Substituted Acrylates.Journal of the American Chemical Society · 2024Article
- Copper-Catalyzed Asymmetric Acylboration of 1,3-Butadienylboronate with Acyl Fluorides.Angewandte Chemie (International ed. in English) · 2023Article
- Asymmetric formal spNature communications · 2023Article
- Intermolecular Metal-Catalyzed C‒C Coupling of Unactivated Alcohols or Aldehydes for Convergent Ketone Construction beyond Premetalated Reagents.ACS catalysis · 2023Article
- Ligand Control in Co-Catalyzed Regio- and Enantioselective Hydroboration: Homoallyl Secondary Boronates via Uncommon 4,3-Hydroboration of 1,3-Dienes.Journal of the American Chemical Society · 2023Article
- Chemodivergent, Regio- and Enantioselective Cycloaddition Reactions between 1,3-Dienes and Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Activator-free single-component Co(I)-catalysts for regio- and enantioselective heterodimerization and hydroacylation reactions of 1,3-dienes. New reduction procedures for synthesis of [L]Co(I)-complexes and comparison toDalton transactions (Cambridge, England : 2003) · 2022Article
- A New Paradigm in Enantioselective Cobalt Catalysis: Cationic Cobalt(I) Catalysts for Heterodimerization, Cycloaddition, and Hydrofunctionalization Reactions of Olefins.Accounts of chemical research · 2021Article
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2 authors at 1 institution in 1 country.
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Abstract
Ketones are among the most widely used intermediates in organic synthesis, and their synthesis from inexpensive feedstocks could be quite impactful. Regio- and enantioselective hydroacylation reactions of dienes provide facile entry into useful ketone-bearing chiral motifs with an additional latent functionality (alkene) suitable for further elaboration. Three classes of dienes, 2- or 4-monosubstituted and 2,4-disubstituted 1,3-dienes, undergo cobalt(I)-catalyzed regio- and enantioselective hydroacylation, giving products with high enantiomeric ratios (er). These reactions are highly dependent on the ligands, and we have identified the most useful ligands and reaction conditions for each class of dienes. 2-Substituted and 2,4-disubstituted dienes predominantly undergo 1,2-addition, whereas 4-substituted terminal dienes give highly enantioselective 4,1- or 4,3-hydroacylation depending on the aldehyde, aliphatic aldehydes giving 4,1-addition and aromatic aldehydes giving 4,3-addition. Included among the substrates are feedstock dienes, isoprene (US$1.4/kg) and myrcene (US$129/kg), and several common aldehydes. We propose an oxidative dimerization mechanism that involves a Co(I)/Co(III) redox cycle that appears to be initiated by a cationic Co(I) intermediate. Studies of reactions using isolated neutral and cationic Co(I) complexes confirm the critical role of the cationic intermediates in these reactions. Enantioselective 1,2-hydroacylation of 2-trimethylsiloxy-1,3-diene reveals a hitherto undisclosed route to chiral siloxy-protected aldols. Finally, facile syntheses of the anti-inflammatory drug (
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