ArticleAngewandte Chemie (International ed. in English)2015
Palladium-Catalyzed Decarbonylative Dehydration for the Synthesis of α-Vinyl Carbonyl Compounds and Total Synthesis of (-)-Aspewentins A, B, and C.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 50 citations in OpenAlex.
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- Enantioselective total syntheses of six natural and two proposed meroterpenoids fromChemical science · 2023Article
- A facile method for Rh-catalyzed decarbonylativeRSC advances · 2021Article
- Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.Angewandte Chemie (International ed. in English) · 2020Review
- Alkene Synthesis by Photocatalytic Chemoenzymatically Compatible Dehydrodecarboxylation of Carboxylic Acids and Biomass.ACS catalysis · 2019Article
- Irradiation-induced palladium-catalyzed decarboxylative desaturation enabled by a dual ligand system.Nature communications · 2018Article
- Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation.Journal of the American Chemical Society · 2018Article
- CO- and HCl-free synthesis of acid chlorides from unsaturated hydrocarbons via shuttle catalysis.Nature chemistry · 2017Article
- Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids.Journal of the American Chemical Society · 2017Article
- Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.Journal of the American Chemical Society · 2017Article
- Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins.Nature communications · 2017Article
- Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents.Organic letters · 2017Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The direct α-vinylation of carbonyl compounds to form a quaternary stereocenter is a challenging transformation. It was discovered that δ-oxocarboxylic acids can serve as masked vinyl compounds and be unveiled by palladium-catalyzed decarbonylative dehydration. The carboxylic acids are readily available through enantioselective acrylate addition or asymmetric allylic alkylation. A variety of α-vinyl quaternary carbonyl compounds are obtained in good yields, and an application in the first enantioselective total synthesis of (-)-aspewentins A, B, and C is demonstrated.
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