ArticleJournal of the American Chemical Society2017
Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 109 citations in OpenAlex.
- Palladium-Catalyzed Hydroarylation ofThe Journal of organic chemistry · 2025Article
- Tungsten-catalyzed stereodivergent isomerization of terminal olefins.Chemical science · 2025Article
- Transforming cyclopropanes to enamides via σ-C-C bond eliminative borylation.Nature communications · 2024Article
- A Neutral PCThe Journal of organic chemistry · 2024Article
- Coordinating activation strategy enables 1,2-alkylamidation of alkynes.Chemical science · 2023Article
- Article
- Ritter-type iodo(iii)amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides.Chemical science · 2021Article
- A Diastereodivergent and Enantioselective Approach toJournal of the American Chemical Society · 2021Article
- Direct Synthesis of Enamides via Electrophilic Activation of Amides.Journal of the American Chemical Society · 2021Article
- Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.The Journal of organic chemistry · 2021Article
- Ligand-dependent stereoselective Suzuki-Miyaura cross-coupling reactions of β-enamido triflates.Beilstein journal of organic chemistry · 2021Article
- A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C-C Coupling in Air.Angewandte Chemie (International ed. in English) · 2020Article
- Chemodivergent synthesis ofRSC advances · 2019Article
- Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis.Angewandte Chemie (International ed. in English) · 2019Article
- Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substitutedChemical science · 2019Article
- Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Enamides represent bioactive pharmacophores in various natural products, and have become increasingly common reagents for asymmetric incorporation of nitrogen functionality. Yet the synthesis of the requisite geometrically defined enamides remains problematic, especially for highly substituted and Z-enamides. Herein we wish to report a general atom economic method for the isomerization of a broad range of N-allyl amides to form Z-di-, tri-, and tetrasubstituted enamides with exceptional geometric selectivity. This report represents the first examples of a catalytic isomerization of N-allyl amides to form nonpropenyl disubstituted, tri- and tetrasubstituted enamides with excellent geometric control. Applications of these geometrically defined enamides toward the synthesis of cis vicinal amino alcohols and tetrasubstituted α-borylamido complexes are discussed.
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Registered trials
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